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Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements.

Abstract:
Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N,O-silylketene aminal of (3S,4E,alphaR)-1-benzyloxy-3-(N-propionyl-N-alpha-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,alphaR)-N-alpha-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in > 92% d.e.; rearrangement of the diastereomeric (3R,4E,alphaR)-(Z)-N,O-silylketene aminal proceeds with low diastereoselectivity.
Publication status:
Published

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Publisher copy:
10.1039/b306323m

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
Chemical communications (Cambridge, England)
Volume:
9
Issue:
17
Pages:
2134-2135
Publication date:
2003-09-05
DOI:
EISSN:
1364-548X
ISSN:
1359-7345
URN:
uuid:e12575f7-1bdd-402c-874f-9bd274e34ad1
Source identifiers:
110538
Local pid:
pubs:110538
Language:
English

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