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Asymmetric synthesis of beta-substituted Baylis-Hillman products via lithium amide conjugate addition

Abstract:

A three-step protocol for the asymmetric synthesis of a range of β-substituted Baylis-Hillman products has been developed. This procedure involves the diastereoselective conjugate addition of lithium (R)-N-methyl-N-(α-methylbenzyl)amide to an α,β-unsaturated ester to generate an N-protected β-amino ester in high de. Subsequent asymmetric aldol reaction via deprotonation with LDA, transmetallation with B(OMe)3 and addition of an aldehyde gives a range of syn-aldol products in moderate to high ...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2007.05.015

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:
63
Issue:
30
Pages:
7036-7046
Publication date:
2007-07-23
DOI:
ISSN:
0040-4020
Language:
English
Pubs id:
pubs:110652
UUID:
uuid:21ed0634-6f65-4f43-bbe1-02fbbcea271c
Local pid:
pubs:110652
Source identifiers:
110652
Deposit date:
2012-12-19

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