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

Abstract:

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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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2010.04.027

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON More from this journal
Volume:
66
Issue:
25
Pages:
4604-4620
Publication date:
2010-06-19
DOI:
ISSN:
0040-4020
Language:
English
Keywords:
Pubs id:
pubs:60701
UUID:
uuid:b84703bb-3c02-45b0-9828-7e4dd887c5ee
Local pid:
pubs:60701
Source identifiers:
60701
Deposit date:
2012-12-19

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