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

Jingxun Yu; Haichen Ma; Hongliang Yao; Hang Cheng; Rongbiao Tong

doi:10.1039/C6QO00034G

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

Jingxun Yu,‡^a Haichen Ma,‡^a Hongliang Yao,^a Hang Cheng^a and Rongbiao Tong*^ab

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* Corresponding authors

^a Department of Chemistry, Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, China
E-mail: rtong@ust.hk

^b HKUST Shenzhen Research Institute, Shenzhen, China

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 S_N2-type cycloacetalization.

This article is part of the themed collection: Celebrating the 75th Birthday of Professor Barry Trost

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DOI: https://doi.org/10.1039/C6QO00034G
Article type: Research Article
Submitted: 21 ⵉⵏⵏ 2016
Accepted: 24 ⵎⴰⵕ 2016
First published: 25 ⵎⴰⵕ 2016

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

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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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Organic Chemistry Frontiers

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

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

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