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C-alkylation of chiral tropane- and homotropane-derived enamines.

Abstract:
The synthesis and alkylation of chiral, nonracemic tropane- and homotropane-derived enamines is examined as an approach to enantioenriched α-alkylated aldehydes. The two bicyclic N auxiliaries, which differ by a single methylene group, give opposite senses of asymmetric induction on alkylation with EtI and provide modestly enantioenriched 2-ethylhexanal (following hydrolysis of the alkylated iminium). The observed stereoselectivity is supported by density functional studies of ethylation for both enamines.
Publication status:
Published

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Publisher copy:
10.1021/jo3025972

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Inorganic Chemistry
Role:
Author
Journal:
Journal of organic chemistry More from this journal
Volume:
78
Issue:
4
Pages:
1508-1518
Publication date:
2013-02-01
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Language:
English
Keywords:
Pubs id:
pubs:375688
UUID:
uuid:6e71e1df-75a6-46d2-b379-d35df72dfe15
Local pid:
pubs:375688
Source identifiers:
375688
Deposit date:
2013-11-17

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