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Use of lithium (alpha-methylbenzyl)allylamide for a formal asymmetric synthesis of thienamycin

Abstract:
The highly stereoselective conjugate addition of lithium (αR)-(α-methylbenzyl)allylamide 3 to (E)-tert-butyl penta-2,4-dienoate 4, followed by a stereoselective aldol reaction with acetaldehyde, are the key steps in the synthesis of the known β-lactam intermediate, (3S,4R)-3-E(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-vinylazetidin-2-one 2, for elaboration to thienamycin and its derivatives.
Publication status:
Published

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Publisher copy:
10.1039/a700216e

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
CHEMICAL COMMUNICATIONS More from this journal
Issue:
6
Pages:
565-566
Publication date:
1997-03-21
DOI:
EISSN:
1364-548X
ISSN:
1359-7345
Pubs id:
pubs:110834
UUID:
uuid:0d09c818-00ff-4252-b190-a71395895f2a
Local pid:
pubs:110834
Source identifiers:
110834
Deposit date:
2012-12-19

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