Issue 3, 2018

Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes

Abstract

A diastereodivergent asymmetric Michael-alkylation reaction between 3-chloro-oxindoles and β,γ-unsaturated-α-ketoesters has been achieved using L-RaPr2/Sc(OTf)3 and L-PrPr2/Mg(OTf)2 metal complexes as catalysts. Both rel-(1R,2S,3R) and rel-(1S,2S,3R) chiral spiro cyclopropane oxindoles were constructed in good yields, diastereoselectivities and ee values. The diastereodivergent control may originate from different alkylation pathways after the Michael addition, with either intramolecular trapping of the aza-ortho-xylylene intermediate or direct SN2 substitution.

Graphical abstract: Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Jun 2017
Accepted
07 Nov 2017
First published
08 Nov 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 688-692

Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes

Y. Kuang, B. Shen, L. Dai, Q. Yao, X. Liu, L. Lin and X. Feng, Chem. Sci., 2018, 9, 688 DOI: 10.1039/C7SC02757E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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