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The dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat: asymmetric synthesis of alpha-vinyl-beta-hydroxycarboxylic acid derivatives and conversion to alpha-ethylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products)

Abstract:

The synthesis of α-vinyl-β-hydroxyesters and α-ethylidene-β-hydroxyesters (β-substituted Baylis-Hillman products) via the dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat is described. High levels of syn-diastereoselectivity (up to >98% de) are observed for the dienolate aldol reaction with boron enolates, generated either directly with Bu2BOTf or by transmetalation of the potassium enolate with B-bromocatecholborane. Cleavage of the resultant syn-aldol products from th...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2009.07.004

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Journal:
TETRAHEDRON
Volume:
65
Issue:
37
Pages:
7837-7851
Publication date:
2009-09-12
DOI:
ISSN:
0040-4020
Source identifiers:
110648
Language:
English
Keywords:
Pubs id:
pubs:110648
UUID:
uuid:16c2ea81-89f7-40ad-b744-c81a44956509
Local pid:
pubs:110648
Deposit date:
2012-12-19

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