Issue 9, 2021

Fe-BPsalan complex catalyzed highly enantioselective Diels–Alder reaction of alkylidene β-ketoesters

Abstract

A practical, highly efficient iron-catalyzed asymmetric Diels–Alder reaction of various alkylidene β-ketoesters with dienes was developed. Both cyclic and acyclic alkylidene β-ketoesters underwent the reaction well with the Fe-BPsalan complex as the catalyst to afford the addition products including estrone analogues in excellent yields, good to high diastereoselectivities and excellent enantioselectivities under mild reaction conditions. DFT calculations revealed the critical role of the steric effect in directing the reaction selectivity.

Graphical abstract: Fe-BPsalan complex catalyzed highly enantioselective Diels–Alder reaction of alkylidene β-ketoesters

Supplementary files

Article information

Article type
Research Article
Submitted
28 Jan 2021
Accepted
03 Mar 2021
First published
08 Mar 2021

Org. Chem. Front., 2021,8, 1910-1917

Fe-BPsalan complex catalyzed highly enantioselective Diels–Alder reaction of alkylidene β-ketoesters

Y. Ping, Y. Zhou, L. Wu, Z. Li, X. Gu, X. Wan, Z. Xu and C. Che, Org. Chem. Front., 2021, 8, 1910 DOI: 10.1039/D1QO00158B

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