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.)....

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Bibliographic Details
Published in:ACS catalysis 2017-11, Vol.7 (11), p.7748-7752
Main Authors: Khan, Imtiaz, Manzotti, Mattia, Tizzard, Graham J, Coles, Simon J, Melen, Rebecca L, Morrill, Louis C
Format: Article
Language:eng
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Summary: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.
ISSN:2155-5435
2155-5435