Issue 27, 2018

Lewis acid catalyzed asymmetric [4+2] cycloaddition of cyclobutenones to synthesize α,β-unsaturated δ-lactones

Abstract

Here we report an efficient asymmetric [4+2] cycloaddition of β,γ-unsaturated α-ketoesters with cyclobutenones. The corresponding products were obtained in good yields (up to 92%) with excellent enantioselectivities (up to 98% ee) and diastereoselectivities (up to >19/1 dr). Moreover, based on the control experiments and previous reports, a possible catalytic cycle was proposed.

Graphical abstract: Lewis acid catalyzed asymmetric [4+2] cycloaddition of cyclobutenones to synthesize α,β-unsaturated δ-lactones

Supplementary files

Article information

Article type
Communication
Submitted
06 Feb 2018
Accepted
08 Mar 2018
First published
09 Mar 2018

Chem. Commun., 2018,54, 3375-3378

Lewis acid catalyzed asymmetric [4+2] cycloaddition of cyclobutenones to synthesize α,β-unsaturated δ-lactones

Q. Yao, H. Yu, H. Zhang, S. Dong, F. Chang, L. Lin, X. Liu and X. Feng, Chem. Commun., 2018, 54, 3375 DOI: 10.1039/C8CC01040D

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