Rhodium-Catalyzed Asymmetric Intramolecular Cyclopropanation of Substituted Allylic Cyanodiazoacetates

• Published in: Advanced synthesis & catalysis Vol. 347; no. 11-13; pp. 1547 - 1552
• Main Authors: Lin, Wei, Charette, André B.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.10.2005; WILEY‐VCH Verlag; Wiley
• Subjects: Chemistry; Chemistry, Applied; Chemistry, Organic; chiral catalyst; cyanodiazoacetates; halocyclopropanes; intramolecular cyclopropanation; Physical Sciences; rhodium; Science & Technology; DIAZOACETATES; ALPHA-DIAZO CARBONYL; DIRHODIUM(II); AMINO-ACIDS; cyanodiazoacetates; halocyclopropanes; BETA-KETO SULFONES; PHENYLALANINE; chiral catalyst; intramolecular cyclopropanation; PHENYLIODONIUM YLIDES; rhodium

A chiral rhodium catalyst, Rh2[4S‐(4′)‐FBNAZ]4, was synthesized and was shown to catalyze the intramolecular cyclopropanation of substituted allylic cyanodiazoacetates. Alkenes bearing an electron‐deficient substituent including carbonyl and halogens are converted into the corresponding cyclopropane...