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Published March 9, 2005 | Supplemental Material
Journal Article Open

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


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.

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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Supplemental Material - ja044054asi20050114_070643.pdf


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