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 | |
Publication status | Published - 3 Nov 2017 |
Keywords
- amino esters
- frustrated Lewis pairs
- metal-free hydrogenation
- sequential catalysis
- stereoselective