Conjugate addition of lithium N-tert-butyldimethylsilyloxy-N-(alpha-methylbenzyl)amide: asymmetric synthesis of beta(2,2,3)-trisubstituted amino acids

Journal article

Conjugate addition of the homochiral ammonia equivalent lithium N-tert-butyldimethylsilyloxy-N-(α-methylbenzyl)amide to a range of α,β-unsaturated esters gives the corresponding β-amino esters in moderate to good levels of diastereoselectivity. O-Desilylation and cyclisation furnishes homochiral isoxazolidin-5-ones in >99:1 dr after purification. Sequential alkylation of these templates proceeds to give the corresponding 3,4-anti-disubstituted and 3,4,4-trisubstituted derivatives as single...

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Authors: Bentley, SA; Davies, S; Lee, J; Roberts, P; Russell, A

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 66
• Issue: 25
• Pages: 4604-4620
• Publication date: 2010-06-19
• DOI: 10.1016/j.tet.2010.04.027
• ISSN: 0040-4020
• Language: English
• Keywords: beta(2,2,3)-Trisubstituted amino acids; Isoxazolidin-5-ones; Homochiral ammonia equivalent; Conjugate addition