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Transition states and origins of 1,4-asymmetric induction in alkylations of 2,2,6-trialkylpiperidine enamines.

Abstract:

The asymmetric C-alkylation of chiral enamines derived from terminal epoxides and lithium 2,2,6-trialkylpiperidides has previously been shown to provide alpha-alkylated aldehydes by intermolecular nucleophilic substitution in good levels of asymmetric induction. We now report a computational study of the origins of asymmetric induction in these reactions. Computational modeling with density functional theory (B3LYP/6-31G(d)) agrees closely with the experimental observations. This stereoselect...

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Publication status:
Published

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Publisher copy:
10.1002/chem.201000046

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Chemistry (Weinheim an der Bergstrasse, Germany)
Volume:
16
Issue:
21
Pages:
6310-6316
Publication date:
2010-06-05
DOI:
EISSN:
1521-3765
ISSN:
0947-6539
URN:
uuid:14204127-6285-4999-ae16-b046275c6916
Source identifiers:
60715
Local pid:
pubs:60715

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