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Frustrated Lewis Pair (FLP)-catalyzed hydrogenation of Aza-Morita–Baylis–Hillman adducts and sequential Organo-FLP catalysis

Khan, Imtiaz, Manzotti, Mattia, Tizzard, Graham J., Coles, Simon J., Melen, Rebecca L. and Morrill, Louis C. 2017. Frustrated Lewis Pair (FLP)-catalyzed hydrogenation of Aza-Morita–Baylis–Hillman adducts and sequential Organo-FLP catalysis. ACS Catalysis 7 (11) , pp. 7748-7752. 10.1021/acscatal.7b03077

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Abstract

Herein we report the metal-free diastereoselective frustrated Lewis pair (FLP)-catalyzed hydrogenation of aza-Morita–Baylis–Hillman (aza-MBH) adducts, accessing a diverse range of stereodefined β-amino acid derivatives in excellent isolated yields (28 examples, 89% average yield, up to 90:10 d.r.). Furthermore, sequential organo-FLP catalysis has been developed. An initial organocatalyzed aza-MBH reaction followed by in situ FLP formation and hydrogenation of the electron-deficient α,β-unsaturated carbonyl compounds can be performed in one-pot, using DABCO as the Lewis base in both catalytic steps.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 2155-5435
Funders: Engineering and Physical Sciences Research Council
Date of First Compliant Deposit: 17 November 2017
Date of Acceptance: 12 October 2017
Last Modified: 26 Mar 2020 15:06
URI: http://orca.cf.ac.uk/id/eprint/106694

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