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Origin of diastereocontrol in the oxy-Michael reactions of delta-lactol anions: a computational and experimental study.

Abstract:

The diastereoselectivity in the alkylation and Michael addition of "naked" 6-substituted delta-lactolates has been studied by density functional (B3LYP) calculations with ab initio (MP2) energy refinements. The resulting proposed model for the origins of stereocontrol in this reaction has been tested by experiment. The reactions lead to a high cis diastereoselectivity across the THP ring due to the preference for both the alkoxide and the 6-substituent to sit equatorial in the alkylation tran...

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Publication status:
Published

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Publisher copy:
10.1002/chem.200801368

Authors


Richardson, RD More by this author
Hernandez-Juan, FA More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Chemistry (Weinheim an der Bergstrasse, Germany)
Volume:
14
Issue:
31
Pages:
9607-9612
Publication date:
2008
DOI:
EISSN:
1521-3765
ISSN:
0947-6539
URN:
uuid:dd614d76-d070-48c8-a62e-92b96b87b91f
Source identifiers:
52067
Local pid:
pubs:52067

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