Issue 6, 2016

Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds

Abstract

Development of two new protocols for oxa-[3 + 2] cycloaddition reactions of Achmatowicz products with 1,3-dicarbonyl compounds for rapid and highly efficient assembly of polycyclic furopyranones is described. Plausible mechanisms were proposed to involve either Pd-catalyzed Tsuji–Trost allylation and concomitant oxa-Michael cyclization or quinine-promoted cascade Michael addition and SN2-type cycloacetalization.

Graphical abstract: Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds

Supplementary files

Article information

Article type
Research Article
Submitted
21 Jän 2016
Accepted
24 Mär 2016
First published
25 Mär 2016

Org. Chem. Front., 2016,3, 714-719

Author version available

Diastereoselective and regiodivergent oxa-[3 + 2] cycloaddition of Achmatowicz products and cyclic 1,3-dicarbonyl compounds

J. Yu, H. Ma, H. Yao, H. Cheng and R. Tong, Org. Chem. Front., 2016, 3, 714 DOI: 10.1039/C6QO00034G

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