Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita-Baylis-Hillman Adducts and Sequential Organo-FLP Catalysis

Imtiaz Khan; Mattia Manzotti; Graham J. Tizzard; Simon J. Coles; Rebecca L. Melen; Louis C. Morrill

doi:10.1021/acscatal.7b03077

Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita-Baylis-Hillman Adducts and Sequential Organo-FLP Catalysis

Imtiaz Khan, Mattia Manzotti, Graham J. Tizzard, Simon J. Coles, Rebecca L. Melen^*, Louis C. Morrill

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

12 Citations (Scopus)

303 Downloads (Pure)

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.

Original language	English
Pages (from-to)	7748-7752
Number of pages	5
Journal	ACS Catalysis
Volume	7
Issue number	11
Early online date	16 Oct 2017
DOIs	https://doi.org/10.1021/acscatal.7b03077
Publication status	Published - 3 Nov 2017

Keywords

amino esters
frustrated Lewis pairs
metal-free hydrogenation
sequential catalysis
stereoselective

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10.1021/acscatal.7b03077Licence: CC BY

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title = "Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita-Baylis-Hillman Adducts and Sequential Organo-FLP Catalysis",

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.",

keywords = "amino esters, frustrated Lewis pairs, metal-free hydrogenation, sequential catalysis, stereoselective",

author = "Imtiaz Khan and Mattia Manzotti and Tizzard, {Graham J.} and Coles, {Simon J.} and Melen, {Rebecca L.} and Morrill, {Louis C.}",

year = "2017",

month = nov,

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doi = "10.1021/acscatal.7b03077",

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volume = "7",

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journal = "ACS Catalysis",

issn = "2155-5435",

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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.; Morrill, Louis C.

In: ACS Catalysis, Vol. 7, No. 11, 03.11.2017, p. 7748-7752.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita-Baylis-Hillman Adducts and Sequential Organo-FLP Catalysis

AU - Khan, Imtiaz

AU - Manzotti, Mattia

AU - Tizzard, Graham J.

AU - Coles, Simon J.

AU - Melen, Rebecca L.

AU - Morrill, Louis C.

PY - 2017/11/3

Y1 - 2017/11/3

N2 - 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.

AB - 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.

KW - amino esters

KW - frustrated Lewis pairs

KW - metal-free hydrogenation

KW - sequential catalysis

KW - stereoselective

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DO - 10.1021/acscatal.7b03077

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