Issue 18, 2018

Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase

Abstract

2-Benzylpyridine N-oxides possessing less acidic α-protons were utilized as pronucleophiles for the first time in enantioselective addition reactions under Brønsted base catalysis. A chiral bis(guanidino)iminophosphorane was able to overcome the inherent issue of low acidity of the pronucleophiles, establishing the diastereo- and enantioselective direct Mannich-type reaction with N-Boc imines. The control experiments indicated that the N-oxide moiety of the substrates played a critical role in achieving the high stereoselectivity.

Graphical abstract: Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase

Supplementary files

Article information

Article type
Edge Article
Submitted
19 feb 2018
Accepted
19 apr 2018
First published
20 apr 2018
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, 4348-4351

Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase

Q. Hu, A. Kondoh and M. Terada, Chem. Sci., 2018, 9, 4348 DOI: 10.1039/C8SC00808F

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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