Issue 54, 2021

Oxyallyl cation promoted dearomative semipinacol rearrangement: a facile stereodivergent synthesis of spiro-indolines with contiguous quaternary centers

Abstract

A novel oxyallyl cation promoted semipinacol rearrangement of indole-type allylic alcohols was disclosed for the stereodivergent synthesis of spiro-indolines. A variety of spiro-indolines were obtained with moderate to good yields. Three contiguous stereocenters, two of which are vicinal quaternary centers, were effectively formed with good diastereoselectivity. It is worth noting that two diastereoisomers of rearranged products can be readily achieved by easily regulating the reaction conditions. This method may provide an applicable approach for the synthesis of natural indole alkaloids.

Graphical abstract: Oxyallyl cation promoted dearomative semipinacol rearrangement: a facile stereodivergent synthesis of spiro-indolines with contiguous quaternary centers

Supplementary files

Article information

Article type
Communication
Submitted
28 Apr 2021
Accepted
04 Jun 2021
First published
05 Jun 2021

Chem. Commun., 2021,57, 6632-6635

Oxyallyl cation promoted dearomative semipinacol rearrangement: a facile stereodivergent synthesis of spiro-indolines with contiguous quaternary centers

Y. Xie, Y. Wang, X. Zhao, A. Wang, Z. Chen and Y. Tu, Chem. Commun., 2021, 57, 6632 DOI: 10.1039/D1CC02033A

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