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 journalArticle (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 languageEnglish
Pages (from-to)7748-7752
Number of pages5
JournalACS Catalysis
Volume7
Issue number11
Early online date16 Oct 2017
DOIs
Publication statusPublished - 3 Nov 2017

Keywords

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

Fingerprint Dive into the research topics of 'Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita-Baylis-Hillman Adducts and Sequential Organo-FLP Catalysis'. Together they form a unique fingerprint.

Cite this