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

Frustrated Lewis Pair (FLP)-catalyzed hydrogenation of aza-Morita–Baylis–Hillman adducts and sequential organo-FLP catalysis
Frustrated Lewis Pair (FLP)-catalyzed hydrogenation of aza-Morita–Baylis–Hillman adducts and sequential organo-FLP catalysis
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.
2155-5435
7748-7752
Khan, Imtiaz
472f2db0-2192-4200-b2a7-9ac4cc798fd9
Manzotti, Mattia
f001e908-c8fb-421a-97a5-e3a50e9998d0
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Melen, Rebecca L.
5f4a2875-7a4b-4eb0-b738-454e5e9b6fdf
Morrill, Louis C.
987789df-0246-46eb-80e0-79075392bb95
Khan, Imtiaz
472f2db0-2192-4200-b2a7-9ac4cc798fd9
Manzotti, Mattia
f001e908-c8fb-421a-97a5-e3a50e9998d0
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Melen, Rebecca L.
5f4a2875-7a4b-4eb0-b738-454e5e9b6fdf
Morrill, Louis C.
987789df-0246-46eb-80e0-79075392bb95

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), 7748-7752. (doi:10.1021/acscatal.7b03077).

Record type: Article

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.

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Accepted/In Press date: 16 October 2017
e-pub ahead of print date: 16 October 2017
Published date: 3 November 2017

Identifiers

Local EPrints ID: 416677
URI: http://eprints.soton.ac.uk/id/eprint/416677
ISSN: 2155-5435
PURE UUID: 12fba9d5-0b3a-4409-aa8d-827de83bc892
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 04 Jan 2018 17:30
Last modified: 26 Nov 2021 02:45

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Contributors

Author: Imtiaz Khan
Author: Mattia Manzotti
Author: Simon J. Coles ORCID iD
Author: Rebecca L. Melen
Author: Louis C. Morrill

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