N-Heterocyclic Carbene-Catalyzed Cyclization of Unsaturated Acyl Chlorides and Ketones

• Published in: Advanced synthesis & catalysis Vol. 353; no. 11-12; pp. 1943 - 1948
• Main Authors: Shen, Li-Tao, Shao, Pan-Lin, Ye, Song
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.08.2011; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Activated; asymmetric catalysis; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Chlorides; cyclization; Derivatives; dihydropyranones; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Ketones; N-heterocyclic carbenes; Optical activity; Organic chemistry; organocatalysis; Physical Sciences; Preparations and properties; Science & Technology; Synthesis; Unsaturated; vinylketenes; HIGHLY ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ACID; asymmetric catalysis; DISUBSTITUTED KETENES; cyclization; 2+2 CYCLOADDITIONS; organocatalysis; NUCLEOPHILIC CARBENES; ALDOL-LACTONIZATION; DIELS-ALDER REACTION; BETA-LACTONES; dihydropyranones; N-heterocyclic carbenes; vinylketenes; DELTA-LACTONES; Catalytic reaction; Nitrogen heterocycle; Organocatalyst; Pyranone derivatives; Oxygen heterocycle; Asymmetric catalysis; Ketone; Ketenes; Unsaturated compound; Cyclization; Vinylic compound; Acyl chloride
• ISSN: 1615-4150; 1615-4169; 1615-4169
• DOI: 10.1002/adsc.201100178

A straightforward synthesis of optically active trifluoromethyl dihydropyranones and spirocyclic oxindole‐dihydropyranones has been realized by the chiral N‐heterocyclic carbenes‐catalyzed cyclization of α,β‐unsaturated β‐methylacyl chlorides with activated trifluoromethyl ketones or isatin derivatives.