Tetrazolic Acid Functionalized Dihydroindol: Rational Design of a Highly Selective Cyclopropanation Organocatalyst
- 22 June 2007
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (15), 5874-5877
- https://doi.org/10.1021/jo070519e
Abstract
Herein we wish to report our development of an improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole (1) for the enantioselective organocatalyzed cyclopropanation of alpha,beta-unsaturated aldehydes with sulfur ylides. The new organocatalyst readily facilitates the enantioselective organocatalytic cyclopropanation, providing cyclized product in excellent diastereoselectivities ranging from 96% to 98% along with enantioselectivities exceeding 99% enantiomeric excess for all reacted alpha,beta-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.Keywords
This publication has 54 references indexed in Scilit:
- Organocatalytic Highly Enantioselective Synthesis of Secondary α-HydroxyphosphonatesOrganic Letters, 2006
- A versatile organocatalyst for the asymmetric conjugate addition of nitroalkanes to enonesChemical Communications, 2005
- Enantioselective Organocatalytic Cyclopropanation via Ammonium YlidesAngewandte Chemie-International Edition, 2004
- Solution and Solid-State Studies of a Chiral Zinc-Sulfonamide Complex Relevant to Enantioselective CyclopropanationsAngewandte Chemie-International Edition, 1998
- Enantioselective Cyclopropanation of Allylic Alcohols Catalyzed by a Chiral Disulfonamide-Aluminum ComplexChemistry Letters, 1994
- Synthesis and biological activity of carboxylic acid replacement analogs of the potent angiotensin converting enzyme inhibitor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-prolineJournal of Medicinal Chemistry, 1985
- Dimethyloxosulfonium Methylide ((CH3)2SOCH2) and Dimethylsulfonium Methylide ((CH3)2SCH2). Formation and Application to Organic SynthesisJournal of the American Chemical Society, 1965
- Homoconjugation and Homoaromaticity. III.1 The 3-Bicyclo [3.1.0]hexyl System2,3Journal of the American Chemical Society, 1961
- 1,2-HexadieneJournal of the American Chemical Society, 1949
- Über ein allgemeines Verfahren der Peptid‐SyntheseBerichte der deutschen chemischen Gesellschaft (A and B Series), 1932