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Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita–Baylis–Hillman Adducts and Sequential Organo-FLP Catalysis
Author(s) -
Imtiaz Khan,
Mattia Manzotti,
Graham J. Tizzard,
Simon J. Coles,
Rebecca L. Melen,
Louis C. Morrill
Publication year - 2017
Publication title -
acs catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.898
H-Index - 198
ISSN - 2155-5435
DOI - 10.1021/acscatal.7b03077
Subject(s) - dabco , chemistry , frustrated lewis pair , adduct , catalysis , lewis acids and bases , baylis–hillman reaction , yield (engineering) , organic chemistry , stereochemistry , combinatorial chemistry , medicinal chemistry , materials science , metallurgy
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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