Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 47, Pages 14036-14039Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507927
Keywords
enantioselective Heck; N,N ligands; palladium; quaternary stereocenters; verapamil
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Funding
- Sao Paulo Research Foundation [2013/07600-3, 2014/00588-0]
- Swiss National Science Foundation
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [13/07600-3] Funding Source: FAPESP
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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.
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