Highly Diastereoselective and Enantioselective Formal [4 + 1] Ylide Annulation for the Synthesis of Optically Active Dihydrofurans

• Published in: Journal of organic chemistry Vol. 73; no. 17; pp. 6909 - 6912
• Main Authors: Zheng, Jun-Cheng, Zhu, Chun-Yin, Sun, Xiu-Li, Tang, Yong, Dai, Li-Xin
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.09.2008; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; SULFUR YLIDES; ORGANOCATALYTIC CYCLOPROPANATION; MEDIATED CYCLOPROPANATION; ENANTIOMERICALLY PURE; ASYMMETRIC-SYNTHESIS; SULFONIUM SALTS; AMINOSULFOXONIUM SALTS; STEREOSELECTIVE-SYNTHESIS; GLYCIDIC AMIDES; MIGRATORY CYCLIZATION; Cesium carbonate; Annelation; Enantioselectivity; Furan derivatives; Selectivity; Diketone; Oxygen heterocycle; Chemical synthesis; Diastereoselectivity; Organic sulfide; Ylide
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo801135j

On the basis of the reactions of camphor-derived sulfur ylide with α-ylidene-β-diketones, highly efficient and selective synthesis of optically active dihydrofurans has been achieved.