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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil

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Author(s):
Oliveira, Caio C. [1, 2] ; Pfaltz, Andreas [1] ; Duarte Correia, Carlos Roque [2]
Total Authors: 3
Affiliation:
[1] Univ Basel, Dept Chem, CH-4056 Basel - Switzerland
[2] Univ Estadual Campinas, Inst Chem, BR-10384612 Sao Paulo - Brazil
Total Affiliations: 2
Document type: Journal article
Source: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION; v. 54, n. 47, p. 14036-14039, NOV 16 2015.
Web of Science Citations: 39
Abstract

We describe herein a highly regio- and enantioselective Pd-catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all-carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine-and pyrazino-oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to > 99:1. Both linear and branched substituents on the olefins were well-tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O-methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil. (AU)

FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 14/00588-0 - Regio and enantioselective Heck-Matsuda reaction with allylic alcohols using non symmetrical ligands
Grantee:Caio Costa Oliveira
Support type: Scholarships abroad - Research Internship - Doctorate