Addition of enantioenriched γ-oxygenated allylic stannanes to N-acyl iminium intermediates: A new synthesis of syn-amino alcohol derivatives

Angewandte Chemie - International Edition

Volumn 39, Issue 5, 2000, Pages 953-956

  Marshall, James A ^a   Gill, Kevin ^a   Seletsky, Boris M ^b  

^a UNIVERSITY OF VIRGINIA   (United States)

^b EISAI RESEARCH INSTITUTE   (United States)

Author keywords

Alcohols; Asymmetric additions; Synthetic methods; Tin

Indexed keywords

ALCOHOL DERIVATIVE; TIN DERIVATIVE;

ARTICLE; DIASTEREOISOMER; ENANTIOMER; OXYGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034599071     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000303)39:5<953::AID-ANIE953>3.0.CO;2-I     Document Type: Article

References (25)

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3. J. A. Marshall, Chem. Rev. 1996, 97, 31-47; J. A. Marshall, G. P. Luke, J. Org. Chem. 1991, 56, 483-485; J. A. Marshall, G. S. Welmaker, J. Org. Chem. 1992, 57, 7158-7163.
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9. (E)-γ-Silyloxy allylic stannanes afford markedly higher syn:anti ratios of adducts compared to their Z isomers in additions to aldehydes: J. A. Marshall, G. S. Welmaker, J. Org. Chem. 1992, 57, 7158-7163; J. A. Marshall, J. A. Jablonowski, L. M. Elliott, J. Org. Chem. 1995, 60, 2662-2663.
10. The corresponding cis-oxazolidinone derived from the anti adduct 4 showed a coupling of 8.0 Hz for these two protons.
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12. Imines of enantioenriched α-phenethylamine afford enantioeniched homoallylic amines upon addition of achiral allylic titanium and boron reagents. These additions proceed by a cyclic transition state: Y. Gao, F. Sato, J. Org. Chem. 1995, 60, 8136-8137; K. Watanabe, K. Ito, S. Itsuno, Tetrahedron: Asymmetry 1995, 6, 1531-1534.
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14. 2 = (R)-or (S)-PhCH(OMc)CO. CAN = cerium ammonium nitrate, BOC = butoxycarhonyl, DMAP = dimethylaminopyridine.
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19. For a recent new approach to the anti isomers, see N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1998, 120, 11798-11799; review: D. J. Ager, I. Parkash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875.
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24. S. Kobayashi, H. Ishitani, M. Ueno, J. Am. Chem. Soc. 1998, 120, 431-432. Both syn and anti adducts could be prepared but the additions were most effective with aromatic aldehydes.
25. M. Horikawa, J. Bush-Petersen, E. J. Corey, Tetrahedron Lett. 1999, 40, 3843-3846. Mixtures of syn and anti adducts were formed, with syn being favored.