Organocatalytic Strategies for the Synthesis of Axially Chiral Compounds

Giorgio Bencivenni

doi:10.1055/s-0034-1378712

Synlett, Table of Contents

Synlett 2015; 26(14): 1915-1922
DOI: 10.1055/s-0034-1378712

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Organocatalytic Strategies for the Synthesis of Axially Chiral Compounds

Giorgio Bencivenni*

Department of Industrial Chemistry ‘Toso Montanari’', School of Science, University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy Email: giorgio.bencivenni2@unibo.it

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Abstract

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Abstract

Atropisomers are compounds in which chirality arises from hindered rotation along the carbon–carbon or carbon–heteroatom single bond. Recently, organocatalysis appeared to be a rapid, valuable, and efficient strategy for their preparation in an enantioselective manner. In this report a general overview of the most important organocatalyzed atroposelective transformations will be given pointing out in particular the specific role played by the catalyst.

1 Dynamic Kinetic Resolution

2 Desymmetrization of Biaryls

3 Direct Synthesis of Biaryls

4 Asymmetric Friedel–Crafts Amination of Naphthols

5 N-Alkylation via Phase-Transfer Catalysis

6 Desymmetrization of N-Arylmaleimides

Key words

atropisomers - organocatalysis - enantioselective synthesis - desymmetrization - dynamic kinetic resolution

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References

References

For detailed reviews, see:

1a Baudoin O. Eur. J. Org. Chem. 2005; 4223
1b Bringmann G, Mortimer AJ. P, Keller PA, Gresser MJ, Garner J, Breuning M. Angew. Chem. Int. Ed. 2005; 44: 5384
1c Bringmann G, Menche D. Acc. Chem. Res. 2001; 34: 615
1d Lipshutz BH, Kayser F, Liu Z.-P. Angew. Chem., Int. Ed. Engl. 1994; 33: 1842
1e Spring DR, Krishnan S, Schreiber SL. J. Am. Chem. Soc. 2000; 122: 5656
1f Surry DS, Su X, Fox DJ, Franckevicius V, Macdonald SJ. F, Spring DR. Angew. Chem. Int. Ed. 2005; 117: 1904
1g Meyers AI, Lutomski KA. J. Am. Chem. Soc. 1982; 104: 879
1h Meyers AI, Himmelsbach RJ. J. Am. Chem. Soc. 1985; 107: 682

2a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
2b Kamikawa K, Uemura M. Synlett 2000; 938
2c Lipshutz BH, Keith JM. Angew. Chem. Int. Ed. 1999; 38: 3530
2d Baudoin O, Décor A, Cesario M, Guéritte F. Synlett 2003; 2009
2e Broutin P.-E, Colobert F. Org. Lett. 2003; 5: 3281
2f Nicolaou KC, Li H, Boddy CN. C, Ramanjulu JM, Yue T.-Y, Natarajan S, Chu X.-J, Bräse S, Rübsam F. Chem. Eur. J. 1999; 5: 2584
2g Cammidge AN, Crépy KV. L. Chem. Commun. 2000; 1723
2h Yin J, Buchwald SL. J. Am. Chem. Soc. 2000; 122: 12051

3 Comprehensive Enantioselective Organocatalysis. Dalko PI. Wiley-VCH; Weinheim: 2013

4a Christie GH, Kenner JH. J. Chem. Soc., Trans. 1922; 121: 614
4b Clayden J, Moran WJ, Edwards PJ, LaPlante SR. Angew. Chem. Int. Ed. 2009; 48: 6398
4c Kozlowski MC, Morgan BJ, Linton EC. Chem. Soc. Rev. 2009; 38: 3193
4d Clayden J, Fletcher SP, McDouall JJ. W, Rowbottom SJ. M. J. Am. Chem. Soc. 2009; 131: 5331
4e Tetrahedron Symposium-in-Print number 103: Atropisomerism; Clayden, J., Ed.; Tetrahedron 2004, 60, 4325–4558.
4f Cozzi PG, Emer E, Gualandi A. Angew. Chem. Int. Ed. 2011; 50: 3847

5a Miyashita A, Yasuda A, Takaya H, Toriumi K, Ito T, Souchi T, Noyori R. J. Am. Chem. Soc. 1980; 102: 7932
5b Rosini C, Franzini L, Raffaelli A, Salvadori P. Synthesis 1992; 503
5c Clayden J. Angew. Chem., Int. Ed. Engl. 1997; 36: 949
5d Clayden J, Johnson P, Pink JH, Helliwell M. J. Org. Chem. 2000; 65: 7033
5e LaPlante SR, Edwards PJ, Fader LD, Jakalian A, Hucke O. ChemMedChem 2011; 6: 505
5f Bringmann G, Gulder T, Gulder TA. M, Breuning M. Chem. Rev. 2011; 111: 563
5g Bhat V, Wang S, Stoltz BM, Virgil SC. J. Am. Chem. Soc. 2013; 135: 16829
5h Perron Q, Alexakis A. Adv. Synth. Catal. 2010; 352: 2611
5i Usanov DL, Yamamoto H. Angew. Chem. Int. Ed. 2010; 49: 8169
5j Aikawa K, Mikami K. Angew. Chem. Int. Ed. 2003; 42: 5458
5k Huang H, Okuno T, Tsuda K, Yoshimura M, Kitamura M. J. Am. Chem. Soc. 2006; 128: 8716
5l Kumarasamy E, Raghunathan R, Jockusch S, Ugrinov A, Sivaguru J. J. Am. Chem. Soc. 2014; 136: 8729
5m Rios R, Jimeno C, Carroll PJ, Walsh PJ. J. Am. Chem. Soc. 2002; 124: 10272

6 Gustafson JL, Lim D, Miller SJ. Science 2010; 328: 1251

7a Martin R, Jäger A, Böhl M, Richter S, Fedorov R, Manstein DJ, Gutzeit HO, Knölker H.-J. Angew. Chem. Int. Ed. 2009; 48: 8042
7b Kende AS, Liebeskind LS. J. Am. Chem. Soc. 1976; 98: 267

8 Barrett KT, Miller SJ. J. Am. Chem. Soc. 2013; 135: 2963
9 Ahmed A, Bragg RA, Clayden J, Lai LW, McCarthy C, Pink JH, Westlund N, Yasin SA. Tetrahedron 1998; 54: 13277
10 Chan V, Kim JG, Jimeno C, Carroll PJ, Walsh PJ. Org. Lett. 2004; 6: 2051
11 Zimmerman HE, Traxler MD. J. Am. Chem. Soc. 1957; 79: 1920
12 Armstrong RJ, Smith MD. Angew. Chem. Int. Ed. 2014; 53: 12822

13a Ooi T, Maruoka K. Angew. Chem. Int. Ed. 2007; 46: 4222
13b Shirakawa S, Maruoka K. Angew. Chem. Int. Ed. 2013; 52: 4312

14 Burnett F, Zahler RE. Chem. Rev. 1951; 49: 273
15 Mori K, Ichikawa Y, Kobayashi M, Shibata Y, Yamanaka M, Akiyama T. J. Am. Chem. Soc. 2013; 135: 3964
16 Link A, Sparr C. Angew. Chem. Int. Ed. 2014; 53: 5458
17 Li G.-Q, Gao H, Keene C, Devonas M, Ess DH, Kürti L. J. Am. Chem. Soc. 2013; 135: 7414
18 Quideau S, Lyvinec G, Marguerit M, Bathany K, Ozanne-Beaudenon A, Buffeteau T, Cavagnat D, Chénedé A. Angew. Chem. Int. Ed. 2009; 48: 4605
19 De C K, Pesciaioli F, List B. Angew. Chem. Int. Ed. 2013; 52: 9293
20 Satyanarayana T, Abraham S, Kagan HB. Angew. Chem. Int. Ed. 2009; 48: 456
21 Curran DP, Qi H, Geib SJ, DeMello NC. J. Am. Chem. Soc. 1994; 116: 3131

22a Brandes S, Bella M, Kjœrsgaard A, Jørgensen KA. Angew. Chem. Int. Ed. 2006; 45: 1147
22b Brandes S, Niess B, Bella M, Prieto A, Overgaard J, Jørgensen KA. Chem. Eur. J. 2006; 12: 6039

23 Shirakawa S, Liu K, Maruoka K. J. Am. Chem. Soc. 2012; 134: 916
24 Di Iorio N, Righi P, Mazzanti A, Mancinelli M, Ciogli A, Bencivenni G. J. Am. Chem. Soc. 2014; 136: 10250
25 Eudier F, Righi P, Mazzanti A, Ciogli A, Bencivenni G. Org. Lett. 2015; 17: 1728
26 Wu L, Bencivenni G, Mancinelli M, Mazzanti A, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 7196