Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides

Muller, Paul; Bolea, Christelle

doi:10.3390/60300258

Scientific article

English

Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides

ContributorsMuller, Paul; Bolea, Christelle

Published inMolecules, vol. 6, no. 3, p. 258-266

Publication date2001

Abstract

The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 5b has been investigated at 0° C in the presence of several chiral ligands. Enantioselectivities vary in the range of 38–72 %, and are higher than those resulting from reaction of the diazo compound 5c at 65° C. The results are consistent with a carbenoid mechanism for Cu-catalyzed decomposition of phenyliodonium ylides.

Keywords

Phenyliodonium ylides
CH insertion
Cu-catalysis
Asymmetric induction

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Funding

Swiss National Science Foundation - 20-52581.97
Swiss National Science Foundation - CHiral2: Asymmetric Induction in Transition Metal Catalyzed Reactions of Carbenes and Nitrenes

Citation (ISO format)

MULLER, Paul, BOLEA, Christelle. Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides. In: Molecules, 2001, vol. 6, n° 3, p. 258–266. doi: 10.3390/60300258