Issue 20, 2019

Diastereoselective bicyclization of enynols via gold catalysis

Abstract

A Au(I)-catalyzed protocol for the cycloisomerizations of enynols into 4.3.0 (hetero)bicycles with complete regio- and diastereoselection is herein described. The sequential bicyclization exploits substrates with a styryl arm, disclosing in turn a reactive pathway that is complementary to the literature reports. The use of a gold(I)–phosphite catalyst allowed for the synthesis of functionalized polycycles under mild conditions, with good yields and low catalyst loadings (1 mol%).

Graphical abstract: Diastereoselective bicyclization of enynols via gold catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
31 Jul 2019
Accepted
05 Sep 2019
First published
06 Sep 2019

Org. Chem. Front., 2019,6, 3584-3588

Diastereoselective bicyclization of enynols via gold catalysis

C. Cecchini, G. Cera, M. Lanzi, L. Marchiò, M. Malacria and G. Maestri, Org. Chem. Front., 2019, 6, 3584 DOI: 10.1039/C9QO00963A

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