Enantioselective synthesis of axially chiral anilides through rhodium-catalyzed [2+2+2] cycloaddition of 1,6-diynes with trimethylsilylynamides

Journal of the American Chemical Society

Volumn 128, Issue 14, 2006, Pages 4586-4587

  Tanaka, Ken ^a   Takeishi, Kenzo ^a   Noguchi, Keiichi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE; RHODIUM; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; OPTICAL RESOLUTION; REACTION ANALYSIS;

EID: 33646053203     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060348f     Document Type: Article

References (22)

1. For the pioneering work on axially chiral N-substituted o-tert-butylanilides, see: Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132.
2. (a) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634-2640.
3. (b) Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295-1304.
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6. For asymmetric synthesis of axially chiral anilides through enantiotopic deprotonation, see: (a) Hata, T.; Koide, H.; Taniguchi, N.; Uemura, M. Org. Lett. 2000, 2, 1907-1910.
7. (b) Bennett, D. J.; Pickering, P. L.; Simpkins, N. S. Chem. Commun. 2004, 1392-1393.
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11. +/modified-BINAP-catalyzed chemo- and regioselective intermolecular alkyne cyclotrimerization, see: (a) Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697-4699.
12. (b) Tanaka, K.; Toyoda, K.; Wada, A.; Shirasaka, K.; Hirano, M. Chem. Eur. J. 2005, 11, 1145-1156.
13. Enantioselective syntheses of axially chiral biaryl compounds through [2+2+2] cycloaddition have been reported. For Co. see: (a) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
14. For Ir, see: (b) Shibata, T.; Fujimoto, T.; Yokota, K.; Takagi, K. J. Am. Chem. Soc. 2004, 126, 8382-8383.
15. For Rh, see: (c) Tanaka, K.; Nishida, G.; Wada, A.; Noguchi, K. Angew. Chem., Int. Ed. 2004, 43, 6510-6512.
16. (d) Tanaka, K.; Nishida, G.; Ogino, M.; Hirano, M.; Noguchi, K. Org. Lett. 2005, 7, 3119-3121.
17. (e) Tanaka, K.; Wada, A.; Noguchi, K. Org. Lett. 2005, 7, 4737-4739.
18. For a recent review of ynamides, see: Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575-7606.
19. Witulski et al. reported the rhodium-catalyzed [2+2+2] cycloaddition of ynamides for the synthesis of nitrogen heterocycles: (a) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430.
20. (b) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281-3284.
21. The ee's of the product anilides derived from ynamide 2f and 1,6-diynes 1a-c,e could not be determined by chiral HPLC analysis.
22. No regioisomer was generated other than 3fa.