Novel Imidazolidine-Tetrazole Organocatalyst for Asymmetric Conjugate Addition of Nitroalkanes
- 9 August 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (18) , 3897-3900
- https://doi.org/10.1021/ol051301m
Abstract
The Michael addition of nitroalkanes to alpha,beta-unsaturated enones catalyzed by a novel chiral imidazolidine-2-yltetrazole organocatalyst has been investigated. The new more soluble organocatalyst decreases reaction times and improves enantioselectivities compared to other catalysts. The Michael addition adducts were obtained with up to 92% ee. [reaction: see text]Keywords
This publication has 26 references indexed in Scilit:
- Enantioselective Organocatalytic Hydride ReductionJournal of the American Chemical Society, 2004
- Highly Enantio‐ and Diastereoselective Organocatalytic Domino Michael‐Aldol Reactions of β‐Diketone and β‐Ketosulfone Nucleophiles with α,β‐Unsaturated KetonesAdvanced Synthesis & Catalysis, 2004
- 5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefinsChemical Communications, 2004
- Highly Enantio‐ and Diastereoselective Organocatalytic Asymmetric Domino Michael–Aldol Reaction of β‐Ketoesters and α,β‐Unsaturated KetonesAngewandte Chemie International Edition in English, 2004
- Organocatalytic Asymmetric Michael Reaction of Cyclic 1,3‐Dicarbonyl Compounds and α,β‐Unsaturated Ketones—A Highly Atom‐Economic Catalytic One‐Step Formation of Optically Active Warfarin AnticoagulantAngewandte Chemie, 2003
- Highly Enantioselective Organocatalytic Conjugate Addition of Malonates toAcyclic α,β‐Unsaturated EnonesAngewandte Chemie International Edition in English, 2003
- Nitro and related groupsJournal of the Chemical Society, Perkin Transactions 1, 2002
- Organocatalytic Asymmetric Conjugate Addition of Nitroalkanes to α,β-Unsaturated Enones Using Novel Imidazoline CatalystsThe Journal of Organic Chemistry, 2002
- The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated AldehydesJournal of the American Chemical Society, 2002
- Functionalized Nitroalkanes as Useful Reagents for Alkyl Anion SynthonsSynthesis, 1988