Issue 3, 2017
From the journal:

Chemical Science

Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters†

Chun Zhang,a   Brandon Tutkowski,b   Ryan J. DeLuca,a   Leo A. Joyce,c   Olaf Wiest ORCID logo b  and  Matthew S. Sigman ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA

b Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA

c Process Research & Development, Merck Research Laboratories, Rahway, New Jersey, USA

Abstract

An enantioselective, redox-relay Heck alkenylation of trisubstituted allylic alkenol substrates has been developed. This process enables the construction of vicinal stereocenters in high diastereo- and enantioselectivity and allows the formation of enolizable α-carbonyl methyl-substituted stereocenters with no observed epimerization under the reported reaction conditions.

Graphical abstract: Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters

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Article information

DOI
https://doi.org/10.1039/C6SC04585E
Article type
Edge Article
Submitted
13 Oct 2016
Accepted
08 Dec 2016
First published
09 Dec 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 2277-2282

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Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters

C. Zhang, B. Tutkowski, R. J. DeLuca, L. A. Joyce, O. Wiest and M. S. Sigman, Chem. Sci., 2017, 8, 2277 DOI: 10.1039/C6SC04585E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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