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BIFUNCTIONAL CHIRAL AUXILIARIES .7. ALDOL REACTIONS OF ENOLATES DERIVED FROM 1,3-DIACYLIMIDAZOLIDINE-2-THIONES AND 1,3-DIACYLIMIDAZOLIDIN-2-ONES

Abstract:

Dibutylboron enolates of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones undergo highly syn-stereoselective aldol reactions with aldehydes to allow elaboration of both acyl sidechains. The reaction is proposed to occur via sequential enolisation rather than via a bisenolate and the stereochemistry of the product was elucidated by both X-ray crystallography and reductive cleavage of a homochiral aldol product to give (1R,2S)-1-phenyl-2-methylpropane-1,3-diol. In contrast, t...

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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:
50
Issue:
22
Pages:
6621-6642
Publication date:
1994-05-30
DOI:
ISSN:
0040-4020
Pubs id:
pubs:110867
UUID:
uuid:6f68ff86-69b5-484b-9d68-80d86d69222b
Local pid:
pubs:110867
Source identifiers:
110867
Deposit date:
2012-12-19

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