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SuperQuat chiral auxiliaries: design, synthesis, and utility

Abstract:

The SuperQuat (4-substituted 5,5-dimethyloxazolidine-2-one) family of chiral auxiliaries was first developed by us in the 1990s to address the shortcomings of the Evans (4-substituted oxazolidin-2-one) family of chiral auxiliaries. The incorporation of geminal dimethyl substitution at C(5) has two effects: (i) it induces a conformational bias on an adjacent, otherwise conformationally labile C(4)-substituent so that it projects towards the N-acyl fragment, thus offering superior diastereofaci...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c8ob02819b

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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Magdalen College
Role:
Author
ORCID:
0000-0003-3181-8748
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
St Catherine's College
Role:
Author
Publisher:
Royal Society of Chemistry
Journal:
Organic and Biomolecular Chemistry More from this journal
Volume:
17
Issue:
6
Pages:
1322-1335
Publication date:
2018-12-19
Acceptance date:
2018-12-18
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Pmid:
30633283
Language:
English
Pubs id:
pubs:959960
UUID:
uuid:f01c49bc-566b-41fe-89d8-7343ac7ab7f5
Local pid:
pubs:959960
Source identifiers:
959960
Deposit date:
2019-01-18

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