Journal article icon

Journal article

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...

Expand abstract
Publication status:
Published

Actions


Access Document


Publisher copy:
10.1039/b604073j

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Expand authors...
Journal:
Organic and biomolecular chemistry
Volume:
4
Issue:
14
Pages:
2753-2768
Publication date:
2006-07-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:62006303-60c3-45ad-8375-4492a1b1b6df
Source identifiers:
110555
Local pid:
pubs:110555

Terms of use


Metrics


Views and Downloads






If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP