Asymmetric synthesis of α-Amino acid derivatives via an electrophilic amination of chiral amide cuprates with Li t-Butyl-N-tosyloxycarbamate

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2817-2820

  Zheng, Nan ^a   Armstrong III, Joseph D ^a   McWilliams, J Christopher ^a   Volante, R P ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031005924     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00477-2     Document Type: Article

References (20)

1. (a) Williams, R. M. Organic Chemistry Series Volume 7: Synthesis of Optically Active a-Amino acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989.
2. (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
3. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488 and references cited therein.
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12. (b) Greck, C.; Bischoff, L.; Girard, A.; Hajicek, J.; Genet, J.P. Bull Soc Chim Fr, 1994, 131, 429.
13. (a) Askin, D.; Eng, K. K.; Rossen, K.; Purick, R. M.; Wells, K. M.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1994, 35, 673.
14. (b) Davies, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7619.
15. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527.
16. McWilliams, J. C.; Armstrong, J. D.; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1996, 118, 11970.
17. 2g was prepared via a two-step sequence. The mixed pivalic acid anhydride, which was generated in situ from the corresponding carboxylic acid, reacted with cis-aminoindanol to give the hydroxyamide. After workup, the isolated hydroxyamide was treated with 2-methoxypropene and PPTS to afford the desired amide 2g.
18. Askin et al. also observed the indeneamide by-product derived from benzylic deprotonation in a similar system. Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2771.
19. The absolute stereochemistry of the compounds as well as their structures were determined unequivocally by the following protocol. The commercially available N-BOC-protected amino acids were coupled with 1S,2R-cis aminoindanol 1 according to the scheme below. The resulting diastereomers were baseline-resolved by HPLC using a Zorbax Rx-C8 reversed-phased column. Conditions for amide formation see: Ho, G. J.; Emerson, K. M.; Mathre, D.; Shuman, R. F.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 3569.
20. 4: C, 71.54 H, 7.39; N, 6.42; found: C, 71.75; H, 7.36; N, 6.34.