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DOI: 10.1055/s-0035-1562793
The Diamino Analogues of Privileged Corey–Bakshi–Shibata and Jørgensen–Hayashi Catalysts: A Comparison of Their Performance
Publication History
Received: 28 June 2016
Accepted: 29 June 2016
Publication Date:
01 September 2016 (online)
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Abstract
α,α-Diarylprolinol derivatives are well-established families of organocatalysts that are widely used to promote diverse asymmetric reactions. The enantioinduction generated from these ligands is mainly due to the gem-diphenyl carbinol fragment. For this reason, the synthesis of diaza analogues seemed an evident and attractive issue to address in the development of alternative chiral ligands. Although the O→N substitution and subsequent derivatization at first glance looked simple, it was necessary to deal with various unexpected synthetic difficulties. It was established that suitable modifications of the side chain in the diaza analogues afford reaction yields and stereoselectivities that are comparable to those exhibited by the amino alcohol analogues. Nevertheless, various potential applications still remain undeveloped.
1 Introduction
2 Oxazaborolidines and Diazaborolidines in Borane-Mediated Reduction of Prochiral Ketones
3 Organocatalyzed Asymmetric Epoxidations
4 Assessing the Organocatalytic Capability of the α,α-Diphenylprolinol Diaza-Analogues through Benchmark Mannich and Michael Reactions
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References
- 1 Kapfhammer J, Matthes A. Z. Physiol. Chem. 1934; 223: 43
- 2a Soai K, Ookawa A, Ogawa K, Kaba T. J. Chem. Soc., Chem. Commun. 1987; 467
- 2b Soai K, Ookawa A, Kaba T, Ogawa K. J. Am. Chem. Soc. 1987; 109: 7111
- 3a Enders D, Eichenauer H. Tetrahedron Lett. 1977; 18: 191
- 3b Enders D, Dhulut S, Steinbusch D, Herrbach A. Chem. Eur. J. 2007; 13: 3942
- 3c Brehme R, Enders D, Fernandez R, Lassaletta JM. Eur. J. Org. Chem. 2007; 5629
- 4 Enders D, Kipphardt H, Gerdes P, Breña-Valle L, Bhushan V. Bull. Soc. Chim. Belg. 1988; 97: 691
- 5 Enders D, Bhushan V. Tetrahedron Lett. 1988; 29: 2437
- 6a Hirao A, Itsuno S, Nakahama S, Yamazaki N. J. Chem. Soc., Chem. Commun. 1981; 315
- 6b Itsuno S, Ito K, Hirao A, Nakahama S. J. Chem. Soc., Chem. Commun. 1983; 469
- 6c Itsuno S, Hirao A, Nakahama S, Yamazaki N. J. Chem. Soc., Perkin Trans. 1 1983; 1673
- 6d Itsuno S, Ito K, Hirao A, Nakahama S. J. Org. Chem. 1984; 49: 555
- 6e Itsuno S, Nakano M, Miyazaki K, Masuda H, Ito K, Hirao A, Nakahama S. J. Chem. Soc., Perkin Trans. 1 1985; 2039
- 6f Itsuno S, Sarukai Y, Ito K, Hirao A, Nakahama S. Bull. Chem. Soc. Jpn. 1987; 60: 395
- 7 Corey EJ, Bakshi RK, Shibata S. J. Am. Chem. Soc. 1987; 109: 5551
- 8a Mathre DJ, Thomson AS, Douglas AW, Hoogsteen K, Carroll JD, Corley EG, Grabowski EJ. J. J. Org. Chem. 1993; 58: 2880
- 8b Salunkhe AM, Burkhardt ER. Tetrahedron Lett. 1997; 38: 1523
- 8c Ortiz-Maciales M, De Jesús M, González E, Raptis RG, Baran P. Acta Crystallogr. 2004; C60: o173
- 9a Corey EJ, Bakshi RK, Shibata S, Chen C.-P, Singh VK. J. Am. Chem. Soc. 1987; 109: 7925
- 9b Corey EJ, Azimiora M, Sarshar S. Tetrahedron Lett. 1992; 33: 3429
- 9c Mathre DJ, Jones TK, Xavier LC, Blacklock TJ, Reamer RA, Mohan JJ, Turne Jones ET, Hoogsteen K, Baum MW, Grabowski EJ. J. J. Org. Chem. 1991; 56: 751
- 10a Jones DK, Liotta DC. J. Org. Chem. 1993; 58: 799
- 10b Alagona G, Ghio C, Persico M, Tomasi S. J. Am. Chem. Soc. 2003; 125: 10027
- 10c Alagona G, Ghio C, Tomasi S. Theor. Chem. Acc. 2004; 111: 287
- 11a Clayden J, Greeves N, Warren S, Wothers P In Organic Chemistry . Oxford University Press; Oxford: 2001: 1235
- 11b Lin G.-Q, Li Y.-M, Chan AS. C In Principles and Applications of Asymmetric Synthesis . Wiley-Interscience; New York: 2001. Chap. 6, 367
- 12a Corey E, Helal CJ. Angew. Chem. Int. Ed. 1998; 37: 1986
- 12b Wallbaum S, Martens J. Tetrahedron: Asymmetry 1992; 3: 1475
- 12c Itsuno S In Comprehensive Asymmetric Catalysis . Vol. I. Jacobsen EN, Pfaltz A, Yamamoto H. Springer Verlag; Berlin: 2000: 351
- 13 Willems JG. H, Dommerholt FJ, Hammink JB, Vaarhorst AM, Thijs L, Zwaneburg B. Tetrahedron Lett. 1995; 36: 603
- 14a Rama Rao AV, Gurjar MK, Kaiwar V. Tetrahedron: Asymmetry 1992; 3: 859
- 14b Behnen W, Dauelsberg C, Wallbaum J, Martens J. Synth. Commun. 1992; 22: 2143
- 15 Rama Rao AV, Gurjar MK, Sharma PA, Kaiwar V. Tetrahedron Lett. 1990; 31: 2341
- 16a Kim YH, Park DH, Byun IS, Yoon IK, Park CS. J. Org. Chem. 1993; 58: 4511
- 16b Martens J, Dauelsberg C, Behnen W, Wallbaum S. Tetrahedron: Asymmetry 1992; 3: 347
- 17 Corey EJ, Link JO. Tetrahedron Lett. 1989; 30: 6275
- 18 Demir AS, Mecitoglu E, Tanyeli C, Gülbeyaz V. Tetrahedron: Asymmetry 1996; 7: 3359
- 19 Corey EJ, Link JO. Tetrahedron Lett. 1990; 31: 601
- 20 Helal CJ, Magriotis PA, Corey EJ. J. Am. Chem. Soc. 1996; 118: 10938
- 21a Cho BT, Chun YS. J. Chem. Soc., Perkin Trans. 1 1999; 2095
- 21b Mahale RD, Chaskar SP, Patil KE, Maipak GC, Gurjar MK. Org. Process Res. Dev. 2012; 16: 710
- 22a Corey EJ, Link JO. Tetrahedron Lett. 1992; 33: 3431
- 22b Corey EJ, Bakshi RK. Tetrahedron Lett. 1990; 31: 611
- 23 Chen C.-P, Prasad K, Repic O. Tetrahedron Lett. 1991; 32: 7175
- 24 Corey EJ, Helal CJ. Tetrahedron Lett. 1996; 37: 5675
- 25a Nicolaou KC, Bertinato P, Piscopio AD, Chakraborty TK, Minowa N. J. Chem. Soc., Chem. Commun. 1993; 619
- 25b Ikoma A, Kobayashi Y. Synlett 2014; 25: 1150
- 26a Simpson AF, Szeto P, Lathbury DC, Gallagher T. Tetrahedron: Asymmetry 1997; 8: 673
- 26b Simpson AF, Bodkin CD, Butts CP, Armitage MA, Gallagher T. J. Chem. Soc., Perkin Trans. 1 2000; 3047
- 27 Corey EJ, Helal CJ. Tetrahedron Lett. 1995; 36: 9153
- 28 Corey EJ, Guzman-Perez A, Lazerwith SE. J. Am. Chem. Soc. 1997; 119: 11769
- 29a Amigoni SJ, Toupet LJ, Le Floc’h YJ. J. Org. Chem. 1997; 62: 6374
- 29b Dumartin H, Le Floc’h Y, Grée R. Tetrahedron Lett. 1994; 35: 6681
- 30 Parker KA, Ledeboer MW. J. Org. Chem. 1996; 61: 3214
- 31 Corey EJ, Cheng X.-M, Cimprich KA, Sarshar S. Tetrahedron Lett. 1991; 32: 6835
- 32 DeNinno MP, Perner RP, Lijewski L. Tetrahedron Lett. 1990; 31: 7415
- 33 Corey EJ, Link JO. J. Am. Chem. Soc. 1992; 114: 1906
- 34 Khrimian AP, Oliver JE, Waters RM, Panicker S, Nicholson JM, Klun JA. Tetrahedron: Asymmetry 1996; 7: 37
- 35 Corey EJ, Helal CJ. Tetrahedron Lett. 1993; 34: 5227
- 37 Corey EJ, Reichard GA. Tetrahedron Lett. 1989; 30: 5207
- 38a Brunel J.-M, Pardigon O, Faure B, Buono G. J. Chem. Soc., Chem. Commun. 1992; 287
- 38b Brunel J.-M, Chiodi O, Faure B, Fotiadu F, Buono G. J. Organomet. Chem. 1997; 529: 285
- 38c Burns B, King NP, Studley JR, Tye H, Wills M. Tetrahedron: Asymmetry 1994; 5: 801
- 39 Froelich O, Bonin M, Quirion J.-C, Husson H.-P. Tetrahedron: Asymmetry 1993; 4: 2335
- 40a Asami M, Sato S, Watanabe H. Chem. Lett. 2000; 990
- 40b Sato S, Watanabe H, Asami M. Tetrahedron: Asymmetry 2000; 11: 4329
- 41a Asami M, Ohno H, Kobayashi S, Mukaiyama T. Bull. Chem. Soc. Jpn. 1978; 51: 1869
- 41b Asami M. Bull. Chem. Soc. Jpn. 1990; 63: 721
- 41c Asami M, Usui K, Higuchi S, Inoue S. Chem. Lett. 1994; 297
- 41d Asami M, Ishizaki T, Inoue S. Tetrahedron: Asymmetry 1994; 5: 793
- 41e Asami M, Inoue S. Bull. Chem. Soc. Jpn. 1997; 70: 1687
- 41f Asami M, Sato S, Honda K, Inoue S. Heterocycles 2000; 52: 1029
- 42 Asami M, Watanabe H, Honda K, Inoue S. Tetrahedron: Asymmetry 1998; 9: 4165
- 43 Basavaiah D, Venkateswara Rao K, Sekhara Reddy B. Tetrahedron: Asymmetry 2006; 17: 1041
- 44 Basavaiah D, Venkateswara Rao K, Sekhara Reddy B. Tetrahedron: Asymmetry 2007; 18: 968
- 45 Olivares-Romero JL, Juaristi E. Tetrahedron 2008; 64: 9992
- 46a Uraguchi D, Sakaki S, Ueki Y, Ito T, Ooi T. Heterocycles 2008; 76: 1081
- 46b Roy HH, Pitchaiah A, Kim M, Hwang IT, Lee K.-I. RSC Adv. 2013; 3: 3526
- 46c Sadu VS, Roy HN, Arigala P, Hwang I.-T, Lee K.-I. Bull. Korean Chem. Soc. 2014; 35: 1605
- 46d Shi Z, Tan B, Leong WW. Y, Zeng X, Lu M, Zhong G. Org. Lett. 2010; 12: 5402
- 46e Vinayagam P, Vishwanath M, Kesavan K. Tetrahedron: Asymmetry 2014; 25: 568 ; correction: Tetrahedron: Asymmetry 2014, 25, 1252.
- 46f Gleeson O, Gun’ko YK, Connon SJ. Synlett 2013; 24: 1728
- 46g Sema HA, Bez G, Karmakar S. Appl. Organomet. Chem. 2014; 28: 290
- 47 Klumpp DA, Aguirre SL, Sanchez GV. Jr, De Leon SJ. Org. Lett. 2001; 3: 2781
- 48 The low enantioinduction may be due to the unsuccessful formation of a diazaborolidine from the N-ethylated derivative. Unpublished observations.
- 49 Hosoda N, Kamito H, Takano M, Takebe Y, Yamaguchi Y, Asami M. Tetrahedron 2013; 69: 1739
- 50 Chauhan MS, Singh S. J. Mol. Catal. A: Chem. 2015; 398: 184
- 51 Shin SH, Baek EH, Hwang G.-S, Ryu DH. Org. Lett. 2015; 17: 4746
- 52 Lee SI, Hwang G.-S, Ryu DH. J. Am. Chem. Soc. 2013; 135: 7126
- 53 Kang BC, Nam DG, Hwang G.-S, Ryu DH. Org. Lett. 2015; 17: 4810
- 54 Mahender Reddy K, Bhimireddy E, Thirupathi B, Breitler S, Yu S, Corey EJ. J. Am. Chem. Soc. 2016; 138: 2443
- 55a Fingerhut A, Serdyuk OV, Tsogoeva SB. Green Chem. 2015; 17: 2042
- 55b Davis RL, Stiller J, Naicker T, Jiang H, Jørgensen KA. Angew. Chem. Int. Ed. 2014; 53: 7406
-
56 Aggarwal VK, Lopin C, Sandrinelli F. J. Am. Chem. Soc. 2003; 125: 7596
- 57a Ho C.-Y, Chen Y.-C, Wong M.-K, Yang D. J. Org. Chem. 2005; 70: 898
- 57b An improved synthesis of (S)-2-(fluorodiphenylmethyl)pyrrolidine (S)-69 can be found in: Sparr C, Tanzer E.-M, Bachmann J, Gilmour R. Synthesis 2010; 1394
- 58a Sparr C, Schweizer WB, Senn HM, Gilmour R. Angew. Chem. Int. Ed. 2009; 48: 3065
- 58b Zimmer LE, Sparr C, Gilmour R. Angew. Chem. Int. Ed. 2011; 50: 11860
- 59 Cf Juaristi E, Notario R. J. Org. Chem. 2016; 81: 1192
- 60a Lattanzi A. Adv. Synth. Catal. 2006; 348: 339
- 60b Lattanzi A, Russo A. Tetrahedron 2006; 62: 12264
- 60c Russo A, Lattanzi A. Eur. J. Org. Chem. 2008; 2767
- 60d Lattanzi A. Chem. Commun. 2009; 1452
- 60e Russo A, Lattanzi A. Synthesis 2009; 1551
- 60f Lattanzi A. Curr. Org. Synth. 2008; 5: 186
- 60g Marqués-López E, Herrera RP. Curr. Org. Chem. 2011; 15: 2311
- 61 Lu X, Liu Y, Sun B, Cindric B, Deng L. J. Am. Chem. Soc. 2008; 130: 8134
- 62 Schmid MB, Zeitler K, Gschwind RM. J. Am. Chem. Soc. 2011; 133: 7065
- 63 Franzén J, Marigo M, Fielenbach D, Wabnitz TC, Kjærsgaard A, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 18296
- 64a Hayashi Y, Samanta S, Itoh T, Ishikawa H. Org. Lett. 2008; 10: 5581
- 64b Itoh T, Ishikawa H, Hayashi Y. Org. Lett. 2009; 11: 3854
- 64c Boeckman RK. Jr, Miller JR. Org. Lett. 2009; 11: 4544
- 64d Urushima T, Yasui Y, Ishikawa H, Hayashi Y. Org. Lett. 2010; 12: 2966
- 64e Hayashi Y, Shomura H, Xu Q, Lear MJ, Sato I. Eur. J. Org. Chem. 2015; 4316
- 64f Boeckman RK. Jr, Biegasiewicz KF, Tusch DJ, Miller JR. J. Org. Chem. 2015; 80: 4030
- 65a Zhao G.-L, Córdova A. Tetrahedron Lett. 2006; 47: 7417
- 65b Ibrahem I, Córdova A. Chem. Commun. 2006; 1760
- 65c Hayashi Y, Okano T, Itoh T, Urushima T, Ishikawa H, Uchimaru T. Angew. Chem. Int. Ed. 2008; 47: 9053
- 65d Fustero S, Mojarrad F, Pérez Carrión MD, Sanz-Cervera JF, Aceña JL. Eur. J. Org. Chem. 2009; 5208
- 65e Gómez-Bengoa E, Maestro M, Mielgo A, Otazo I, Palomo C, Velilla I. Chem. Eur. J. 2010; 16: 5333
- 65f Galzerano P, Agostino D, Bencivenni G, Sambri L, Bartoli G, Melchiorre P. Chem. Eur. J. 2010; 16: 6069
- 65g Kumaraswamy G, Jayaprakash N, Sridhar B. J. Org. Chem. 2010; 75: 2745
- 65h Urushima T, Ishikawa H, Hayashi Y. Chem. Eur. J. 2011; 17: 8273
- 65i Gómez-Bengoa E, Jiménez J, Lapuerta I, Mielgo A, Oiarbide M, Otazo I, Velilla I, Vera S, Palomo C. Chem. Sci. 2012; 3: 2949
- 65j Hayashi Y, Sakamoto D, Shomura H, Hashizume D. Chem. Eur. J. 2013; 19: 7678
- 65k Meyer D, Marti R, Seebach D. Eur. J. Org. Chem. 2015; 4883
- 66a Zu L, Li H, Wang J, Yub X, Wang W. Tetrahedron Lett. 2006; 47: 5131
- 66b García-García P, Ladépêche A, Halder R, List B. Angew. Chem. Int. Ed. 2008; 47: 4719
- 66c Hayashi Y, Itoh T, Ohkubo M, Ishikawa H. Angew. Chem. Int. Ed. 2008; 47: 4722
- 66d Zheng Z, Perkins BL, Ni B. J. Am. Chem. Soc. 2010; 132: 50
- 66e Mager I, Zeitler K. Org. Lett. 2010; 12: 1480
- 66f Wang L, Zhang X, Ma D. Tetrahedron 2012; 68: 7675
- 66g Wang C, Yang X, Enders D. Chem. Eur. J. 2012; 18: 4832
- 66h Chen J, Geng Z.-C, Li N, Huang X.-F, Pan F.-F, Wang X.-W. J. Org. Chem. 2013; 78: 2362
- 66i Chen H, Zhang D, Xue F, Qin Y. Tetrahedron 2013; 69: 3141
- 66j Feu KS, De la Torre AF, Silva S, De Moraes MA. F. Jr, Corrêa AG, Paixão MW. Green Chem. 2014; 16: 3169
- 66k Lou Y, Xu Y, Chai Z, Shao X, Zhao G, Li Z. Tetrahedron 2015; 71: 6651
- 67a Fan X, Sayalero S, Pericàs MA. Adv. Synth. Catal. 2012; 354: 2971
- 67b Palomo C, Vera S, Velilla I, Mielgo A, Gómez-Bengoa E. Angew. Chem. Int. Ed. 2007; 46: 8054
- 68a Marigo M, Wabnitz TC, Fielenbach D, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 44: 794
- 68b Marigo M, Fielenbach D, Braunton A, Kjærsgaard A, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 44: 3703
- 68c Hayashi Y, Gotoh H, Hayashi T, Shoji M. Angew. Chem. Int. Ed. 2005; 44: 4212
- 68d Marigo M, Schulte T, Franzén J, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 15710
- 68e Zhuang W, Marigo M, Jørgensen KA. Org. Biomol. Chem. 2005; 3: 3883
- 69a Ibrahem I, Santoro S, Himo F, Córdova A. Adv. Synth. Catal. 2011; 353: 245
- 69b Lin S, Deiana L, Zhao G.-L, Sun J, Córdova A. Angew. Chem. Int. Ed. 2011; 50: 7624
- 69c Riguet E. J. Org. Chem. 2011; 76: 8143
- 69d Weng J, Li J.-M, Li F.-Q, Xie Z.-S, Lu G. Adv. Synth. Catal. 2012; 354: 1961
- 69e Pou A, Moyano A. Eur. J. Org. Chem. 2013; 3103
- 70a ‘The Diarylprolinol Silyl Ethers: Ten Years After’: Donslund BS, Johansen TK, Poulsen PH, Haskov KS, Jørgensen KA. Angew. Chem. Int. Ed. 2015; 54: 13860
- 70b ‘Merging Transition-Metal Activation and Aminocatalysis’: Meazza M, Ríos R. Synthesis 2016; 48: 960
- 70c ‘Combined Asymmetric Aminocatalysis and Carbene Catalysis’: Gu J, Du W, Chen Y.-C. Synthesis 2015; 47: 3451
- 70d ‘Enantioselective Organocatalyzed Domino Synthesis of Six-Membered Carbocycles’: Goudedranche S, Raimondi W, Bugaut X, Constantineux T, Bonne D. Synthesis 2013; 45: 1909
- 71 Bertelsen S, Jørgensen KA. Chem. Soc. Rev. 2009; 38: 2178
- 72a Pihko PM, Majander I, Erkkilä A. Top. Curr. Chem. 2010; 291: 29
- 72b Kano T, Mii H, Maruoka K. J. Am. Chem. Soc. 2009; 131: 3450
- 72c Kano T, Shirozu F, Maruoka K. Org. Lett. 2014; 16: 1530
- 72d Bauer JO, Stiller J, Marqués-López E, Strohfeldt K, Christmann M, Strohmann C. Chem. Eur. J. 2010; 16: 12553
- 73 Chi Y, Gellman SH. J. Am. Chem. Soc. 2006; 128: 6804
- 74 Ibrahem I, Zhao G.-L, Córdova A. Chem. Eur. J. 2007; 13: 683
- 75a Vicario JL, Badía D, Carrillo L. Synthesis 2007; 2065
- 75b Kürti L, Czakó B In Strategic Applications of Named Reactions in Organic Synthesis. Elsevier; Amsterdam: 2005: 286
- 76 Blarer SJ, Schweizer WB, Seebach D. Helv. Chim. Acta 1982; 65: 1637
- 77 List B, Pojarliev P, Martin HJ. Org. Lett. 2001; 3: 2423
- 78 Betancort JM, Barbas III CF. Org. Lett. 2001; 3: 3737
- 79 Reyes-Rangel G, Vargas-Caporali J, Juaristi E. Tetrahedron 2016; 72: 379
- 80 See: Jung ME, Piizzi G. Chem. Rev. 2005; 105: 1735
- 81 Mečiarová M, Toma Š, Šebesta R. Tetrahedron: Asymmetry 2009; 20: 2403
- 82 See: Hernández JG, Juaristi E. Chem. Commun. 2012; 48: 5396
For more recent reports, see:
For excellent reviews regarding enantioselective reduction of ketones with chiral oxazaborolidines employed as catalysts, and mechanistic considerations, see:
Also in 2008, Ooi and co-workers described the preparation of several chiral diamines derived from l-valine, l-isoleucine, and l-tert-leucine via azidation of the corresponding diarylamino alcohols:
Furthermore, some years later Lee and co-workers prepared a series of chiral amino azides, employing a biphasic reaction media of H2SO4/toluene:
Other groups have also evaluated (S)-2-(azidodiphenylmethyl)pyrrolidine and derivatives:
Varied reports from diverse research groups:
Interesting and innovative applications are compiled in the following reviews:
Other pyrrolidine derivatives with bulky substituents in the 2-position also directs the enamine attack from the opposite face such as 2-tritylpyrrolidine described in: