Asymmetric Synthesis of 4,5,6- and 3,4,5,6-Substituted Azepanes by a Highly Diastereoselective and Enantioselective Lithiation−Conjugate Addition Sequence
Authors:
- 1 February 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (7) , 2178-2179
Abstract
Asymmetric syntheses of 4,5,6- and 3,4,5,6-substituted azepanes have been achieved by highly diastereoselective and enantioselective (−)-sparteine-mediated asymmetric lithiation−conjugate additions of N-Boc-N-(p-methoxyphenyl)-2,3-substituted allylamines to a β-aryl α,β-unsaturated ester followed by hydrolysis, cyclization, and reduction. Access to the enantiomeric adduct is provided by an invertive lithiation−stannylation−lithiation sequence.Keywords
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