Frustrated Lewis pair (FLP)-catalyzed hydrogenation of aza-Morita–Baylis–Hillman adducts and sequential organo-FLP catalysis

Khan, Imtiaz, Manzotti, Mattia ORCID: https://orcid.org/0000-0001-9058-8087, Tizzard, Graham J., Coles, Simon J., Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 and Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531 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:	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:	05 May 2023 07:03
URI:	https://orca.cardiff.ac.uk/id/eprint/106694

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