Journal article

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

Abstract:: The doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangement of silylketene aminals derived from 5-substituted (3S,4E,alphaR)-1-benzyloxy-3-[N-acyl-N-(alpha-methylbenzyl)amino]pent-4-enes furnishes 2,3-disubstituted (R)-N-alpha-methylbenzyl (2S,3R,4E)-7-benzyloxyhept-4-enamides in >90% de under the "matched" control of both stereogenic centres. Rearrangement of the "mismatched" diastereomeric (3R,4E,alphaR)-substrates proceeds with low diastereoselectivity. The substrate scope of the doubly diastereoselective rearrangement of the "matched" substrates in which two new stereogenic centres are created has been delineated.

Publication status:: Published

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APA Style

Davies, S., Garner, A., Nicholson, R., Osborne, J., Roberts, P., Savory, E., Smith, A., & Thomson, J. (2009). Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. Organic and Biomolecular Chemistry, 7(12), 2604–2611.

MLA Style

Davies, S, et al. “Doubly Diastereoselective [3,3]-Sigmatropic Aza-Claisen Rearrangements.” Organic and Biomolecular Chemistry, vol. 7, no. 12, 2009, pp. 2604–11.

Chicago Style

Davies, S, A Garner, R Nicholson, et al. 2009. “Doubly Diastereoselective [3,3]-Sigmatropic Aza-Claisen Rearrangements.” Organic and Biomolecular Chemistry 7 (12): 2604–11.
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Publisher copy:: 10.1039/b902753j

Authors

+ Davies, S More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Garner, A More by this author

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+ Nicholson, R More by this author

Role:: Author

+ Osborne, J More by this author

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+ Roberts, P More by this author

Role:: Author

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Journal:: Organic and biomolecular chemistry More from this journal
Volume:: 7
Issue:: 12
Pages:: 2604-2611
Publication date:: 2009-06-01
DOI:: 10.1039/b902753j
EISSN:: 1477-0539
ISSN:: 1477-0520

Language:: English
Pubs id:: pubs:110565
UUID:: uuid:d7c1b761-6353-4263-a276-fc654f14a5c4
Local pid:: pubs:110565
Source identifiers:: 110565
Deposit date:: 2012-12-19
ARK identifier:: ark:/29072/ora_d7c1b76163534263a276fc654f14a5c4

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Copyright date:: 2009

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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