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Oxazinanones as chiral auxiliaries: synthesis and evaluation in enolate alkylations and aldol reactions.

Abstract:

Homochiral beta-amino esters (prepared on multigram scale by lithium amide conjugate addition) are readily transformed into oxazinanones. N-acyl derivatives of oxazinanones undergo stereoselective enolate alkylation reactions, with higher stereoselectivities observed for the enolate alkylation of (R)-N-propanoyl-4-iso-propyl-6,6-dimethyl-oxazinan-2-one than the corresponding Evans oxazolidin-2-one. A C(4)-iso-propyl stereodirecting group within the oxazinanone conveys higher stereoselectivity...

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Publication status:
Published

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Publisher copy:
10.1039/b604073j

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Journal:
Organic and biomolecular chemistry
Volume:
4
Issue:
14
Pages:
2753-2768
Publication date:
2006-07-01
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Source identifiers:
110555
Language:
English
Keywords:
Pubs id:
pubs:110555
UUID:
uuid:62006303-60c3-45ad-8375-4492a1b1b6df
Local pid:
pubs:110555
Deposit date:
2012-12-19

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