Issue 28, 2020

Construction of chiral chroman scaffolds via catalytic asymmetric (4 + 2) cyclizations of para-quinone methide derivatives with 3-vinylindoles

Abstract

A catalytic asymmetric (4 + 2) cyclization of ortho-hydroxyphenyl-substituted para-quinone methide derivatives with 3-vinylindoles has been established in the presence of chiral phosphoric acid, which provides a series of chiral chroman derivatives bearing an indole moiety in generally high yields (up to 97%), and with good enantioselectivities (up to 90% ee) and moderate to good diastereoselectivities (up to 95 : 5 dr). This reaction has not only fulfilled the need of developing catalytic asymmetric (4 + 2) cyclizations of para-quinone methide derivatives with electron-rich alkenes, but also provided a useful method for constructing chiral chroman scaffolds.

Graphical abstract: Construction of chiral chroman scaffolds via catalytic asymmetric (4 + 2) cyclizations of para-quinone methide derivatives with 3-vinylindoles

Supplementary files

Article information

Article type
Paper
Submitted
20 May 2020
Accepted
25 Jun 2020
First published
25 Jun 2020

Org. Biomol. Chem., 2020,18, 5388-5399

Construction of chiral chroman scaffolds via catalytic asymmetric (4 + 2) cyclizations of para-quinone methide derivatives with 3-vinylindoles

S. Wu, M. Tu, Q. Hang, S. Zhang, H. Ding, Y. Zhang and F. Shi, Org. Biomol. Chem., 2020, 18, 5388 DOI: 10.1039/D0OB01049A

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