Switching Enantioface Selection in the Asymmetric Nitro-Mannich Reaction Using Single Chiral Bis(imidazolidine)pyridine–Metal Catalysts

Takayoshi Arai; Eri Matsumura

doi:10.1055/s-0034-1378204

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(12): 1776-1780
DOI: 10.1055/s-0034-1378204

letter

Switching Enantioface Selection in the Asymmetric Nitro-Mannich Reaction Using Single Chiral Bis(imidazolidine)pyridine–Metal Catalysts

Takayoshi Arai*

Department of Chemistry, Graduate School of Science, Chiba University, Inage 263-8522, Japan Fax: +81(43)2902889 eMail: tarai@faculty.chiba-u.jp

,

Eri Matsumura

Department of Chemistry, Graduate School of Science, Chiba University, Inage 263-8522, Japan Fax: +81(43)2902889 eMail: tarai@faculty.chiba-u.jp

› Institutsangaben

Abstract

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Abstract

Switching enantioface selection of imines in the metal-catalyzed nitro-Mannich reaction was accomplished with the same enantiomer of diamine-derived bis(imidazolidine)pyridine (PyBidine) ligand. The (S,S)-PyBidine–CoCl₂ complex catalyzed the nitro-Mannich reaction of N-Ts imines to give S-enriched adducts, while the Ni(OAc)₂ complex using the same ligand catalyzed the nitro-Mannich reaction of N-Boc imines in an R-stereoselective manner.

Key words

asymmetric catalysis - chirality - nitro-Mannich - imines - metal salts

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Referenzen

References

Reviews of enantiofacial switching:

1a Sibi MP, Liu M. Curr. Org. Chem. 2001; 5: 719
1b Zanoni G, Castronovo F, Franzini M, Vidari G, Giannini E. Chem. Soc. Rev. 2003; 32: 115
1c Tanaka T, Hayashi M. Synthesis 2008; 3361
1d Bartók M. Chem. Rev. 2010; 110: 1663
1e Escorihuela J, Burguete MI, Luis SV. Chem. Soc. Rev. 2013; 42: 5595

Recent examples of enantiofacial switching:

2a Sohtome Y, Yamaguchi T, Tanaka S, Nagawasa K. Org. Biomol. Chem. 2013; 11: 2780
2b Garzan A, Jaganathan A, Marzijarani NS, Yousefi R, Whitehead DC, Jackson JE, Borhan B. Chem. Eur. J. 2013; 19: 9015
2c Fukata Y, Asano K, Matsubara S. J. Am. Chem. Soc. 2013; 135: 12160

3 Henry L. Bull. Acad. R. Belg. 1896; 32: 33
4 Noble A, Anderson JC. Chem. Rev. 2013; 113: 2887
5 Marqués-López E, Merino P, Tejero T, Herrera RP. Eur. J. Org. Chem. 2009; 2401 ; see also ref. 3
6 Yamada K.-i, Harwood SJ, Gröger H, Shibasaki M. Angew. Chem. Int. Ed. 1999; 38: 3504

Catalytic asymmetric nitro-Mannich reaction using Cu complex:

7a Knudsen KR, Risgaard T, Nishiwaki N, Gothelf KV, Jørgensen KA. J. Am. Chem. Soc. 2001; 123: 5843
7b Nishiwaki N, Knudsen KR, Gothelf KV, Jørgensen KA. Angew. Chem. Int. Ed. 2001; 40: 2992
7c Lee A, Kim W, Lee J, Hyeon T, Kim BM. Tetrahedron: Asymmetry 2004; 15: 2595
7d Knudsen KR, Rahbek K, Jørgensen KA. Org. Biomol. Chem. 2005; 3: 1362
7e Anderson JC, Howell GP, Lawrence RM, Wilson CS. J. Org. Chem. 2005; 70: 5665
7f Zhou H, Peng D, Qin B, Hou Z, Liu X, Feng X. J. Org. Chem. 2007; 72: 10302
7g Tan C, Liu X, Wang L, Wang J, Feng X. Org. Lett. 2008; 10: 5305
7h Zhang G, Yashima E, Woggon W.-D. Adv. Synth. Catal. 2009; 351: 1255
7i Blay G, Escamilla A, Hernández-Olmos V, Pedro JR, Sanz-Marco A. Chirality 2012; 24: 441
7j Choudhary MK, Das A, Kureshy RI, Kumar M, Khan NH, Abdi SH. R, Bajaj HC. Catal. Sci. Technol. 2014; 4: 548

Catalytic asymmetric nitro-Mannich reaction using Zn complex:

8a Gao F, Zhu J, Tang Y, Deng M, Qian C. Chirality 2006; 18: 741
8b Palomo C, Oiarbide M, Halder R, Laso A, López R. Angew. Chem. Int. Ed. 2006; 45: 117
8c Trost BM, Lupton DW. Org. Lett. 2007; 9: 2023

9 Catalytic asymmetric nitro-Mannich reaction using Ni complex: Chen Z, Morimoto H, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2008; 130: 2170

Catalytic asymmetric nitro-Mannich reaction using heterobimetallic system:

10a Yamada K.-I, Moll G, Shibasaki M. Synlett 2001; 980
10b Handa S, Gnanadesikan V, Matsunga S, Shibasaki M. J. Am. Chem. Soc. 2007; 129: 4900
10c Nitabaru T, Kumagai N, Shibasaki M. Molecules 2010; 15: 1280
10d Handa S, Gnanadesikan V, Matsunga S, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 4925

Representative examples of catalytic asymmetric nitro-Mannich reaction using organocatalyst:

11a Okino T, Nakamura S, Furukawa T, Takemoto Y. Org. Lett. 2004; 6: 625
11b Nugent BM, Yoder RA, Johnston JN. J. Am. Chem. Soc. 2004; 126: 3418
11c Yoon TP, Jacobsen EN. Angew. Chem. Int. Ed. 2005; 44: 466
11d Fini F, Sgarzani V, Pettersen D, Herrera RP, Bernardi L, Ricci A. Angew. Chem. Int. Ed. 2005; 44: 7975
11e Palomo C, Oiarbide M, Laso A, López R. J. Am. Chem. Soc. 2005; 127: 17622
11f Singh A, Yoder RA, Shen B, Johnston JN. J. Am. Chem. Soc. 2007; 129: 3466
11g Robak MT, Trincado M, Ellman JA. J. Am. Chem. Soc. 2007; 129: 15110
11h Rueping M, Antonchick AP. Org. Lett. 2008; 10: 1731
11i Wang C, Zhou Z, Tang C. Org. Lett. 2008; 10: 1707
11j Singh A, Johnston JN. J. Am. Chem. Soc. 2008; 130: 5866
11k Gomez-Bengoa E, Linden A, López R, Múgica-Mendiola I, Oiarbide M, Palomo C. J. Am. Chem. Soc. 2008; 130: 7955
11l Wang C.-J, Dong X.-Q, Zhang Z.-H, Xue Z.-Y, Teng H.-L. J. Am. Chem. Soc. 2008; 130: 8606
11m Uraguchi D, Koshimoto K, Ooi T. J. Am. Chem. Soc. 2008; 130: 10878
11n Han B, Liu Q.-P, Li R, Tian X, Xiong X.-F, Deng J.-G, Chen Y.-C. Chem. Eur. J. 2008; 14: 8094
11o Wilt JC, Pink M, Johnston JN. Chem. Commun. 2008; 4177
11p Davis TA, Wilt JC, Johnston JN. J. Am. Chem. Soc. 2010; 132: 2880
11q Davis TA, Johnston JN. Chem. Sci. 2011; 2: 1076
11r Xie H, Zhang Y, Zhang S, Chen X, Wang W. Angew. Chem. Int. Ed. 2011; 50: 11773
11s Wei Y, He W, Liu Y, Liu P, Zhang S. Org. Lett. 2012; 14: 704
11t Johnson KM, Rattley MS, Sladojevich F, Barber DM, Nuñez MG, Goldys AM, Dixon DJ. Org. Lett. 2012; 14: 2492
11u Parra A, Alfaro R, Marzo L, Moreno-Carrasco A, García Ruano JL, Alemán J. Chem. Commun. 2012; 48: 9759
11v Cao D, Chai Z, Zhang J, Ye Z, Xiao H, Wang H, Chen J, Wu X, Zhao G. Chem. Commun. 2013; 49: 5972
11w Núñez MG, Farley AJ. M, Dixon DJ. J. Am. Chem. Soc. 2013; 135: 16348

12a Arai T, Mishiro A, Yokoyama N, Suzuki K, Sato H. J. Am. Chem. Soc. 2010; 132: 5338
12b Arai T, Kajikawa S, Matsumura E. Synlett 2013; 24: 2045

13 Arai T, Mishiro A, Matsumura E, Awata A, Shirasugi M. Chem. Eur. J. 2012; 18: 11219
14 Nishiyama H, Sakaguchi H, Nakamura T, Horihata M, Kondo M, Itoh K. Organometallics 1989; 8: 846
15 Bhor S, Anilkumar G, Tse MK, Klawonn M, Döbler C, Bitterlich B, Grotevendt A, Beller M. Org. Lett. 2005; 7: 3393

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