Issue 15, 2021

Enantioselective hydrogenation of annulated arenes: controlled formation of multiple stereocenters in adjacent rings

Abstract

We report a method for the enantioselective hydrogenation of annulated arenes using 4H-pyrido[1,2-a]pyrimidinones as substrates. The method selectively generates multiple stereocenters in adjacent rings leading to architecturally complex motifs, which resemble bioactive molecules. The mechanistic study of the stereochemical outcome revealed that the catalyst is able to overcome substrate stereocontrol providing all-cis-substituted products predominantly. In a sequential protocol, a matching interaction between catalyst and substrate stereocontrol is achieved that facilitates diastereo- and enantioselective access to trans-products.

Graphical abstract: Enantioselective hydrogenation of annulated arenes: controlled formation of multiple stereocenters in adjacent rings

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Dec 2020
Accepted
03 Mar 2021
First published
04 Mar 2021
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., 2021,12, 5611-5615

Enantioselective hydrogenation of annulated arenes: controlled formation of multiple stereocenters in adjacent rings

M. P. Wiesenfeldt, D. Moock, D. Paul and F. Glorius, Chem. Sci., 2021, 12, 5611 DOI: 10.1039/D0SC07099H

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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