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Highly Selective 1,3-Isomerization of Allylic Alcohols via Rhenium Oxo Catalysis

Morrill, Christie and Grubbs, Robert H. (2005) Highly Selective 1,3-Isomerization of Allylic Alcohols via Rhenium Oxo Catalysis. Journal of the American Chemical Society, 127 (9). pp. 2842-2843. ISSN 0002-7863. doi:10.1021/ja044054a. https://resolver.caltech.edu/CaltechAUTHORS:20170420-084321132

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Abstract

Two reaction strategies are developed to promote the highly selective 1,3-isomerization of a variety of allylic alcohols using O_3ReOSiPh_3 as a catalyst. The first strategy utilizes substrates whose 1,3-regioisomer contains a conjugated alkene, which relies on thermodynamics to obtain high selectivity. The second strategy employs N,O-bis(trimethylsilyl)acetamide as an additive to selectively and irreversibly remove the product from the reaction equilibrium and works well for the isomerization of tertiary allylic alcohols into primary allylic alcohols containing trisubstituted alkene components. High stereoselectivity is also observed in the 1,3-isomerization of enantioenriched allylic alcohols.


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http://dx.doi.org/10.1021/ja044054aDOIArticle
http://pubs.acs.org/doi/full/10.1021/ja044054aPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja044054aPublisherSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2005 American Chemical Society. Received 29 September 2004. Published online 10 February 2005. Published in print 9 March 2005. The authors thank the National Institutes of Health for financial support, Professor Brian M. Stoltz and Professor David MacMillan for suggestions concerning the usage of silicon protecting groups, and Dr. Brian T. Connell, Dr. Anna G. Wenzel, and especially Dr. Gregory L. Beutner for helpful suggestions and insight.
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Issue or Number:9
DOI:10.1021/ja044054a
Record Number:CaltechAUTHORS:20170420-084321132
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170420-084321132
Official Citation:Highly Selective 1,3-Isomerization of Allylic Alcohols via Rhenium Oxo Catalysis Christie Morrill and Robert H. Grubbs Journal of the American Chemical Society 2005 127 (9), 2842-2843 DOI: 10.1021/ja044054a
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76752
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Apr 2017 18:53
Last Modified:15 Nov 2021 17:02

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