Baylis-Hillman Reactions of Sulfonyl Aldimines or Aryl Aldehydes with 3-Methylpenta-3,4-dien-2-one or 3-Benzylpenta-3,4-dien-2-one

• Published in: Chinese journal of chemistry Vol. 25; no. 6; pp. 828 - 835
• Main Author: 施敏 郭英文 李红斌
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.06.2007; WILEY‐VCH Verlag; Wiley
• Subjects: 3-benzylpenta-3; 3-methylpenta-3; 3‐benzylpenta‐3,4‐ dien‐2‐one; 3‐methylpenta‐3,4‐dien‐2‐one; 4- dien-2-one; Baylis-Hillman reaction; Baylis-Hillman反应; Chemistry; Chemistry, Multidisciplinary; chiral catalyst TQO; diastereoselectivity; Physical Sciences; Science & Technology; TQO; 甲基联烯酮; 磺酰亚胺; 芳香醛; 苄基联烯酮; MECHANISM; 3-methylpenta-3,4-dien-2-one; IMINES; 3-benzylpenta-3,4-dien-2-one; ACRYLATE; diastereoselectivity; METHYL VINYL KETONE; Baylis-Hillman reaction; chiral catalyst TQO; DERIVATIVES; ACTIVATED OLEFINS
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.200790152

The attempted Baylis-Hillman reactions of sulfonyl aldimines or aryl aldehydes with 3-methylpenta-3,4-dien-2-one or 3-benzylpenta-3,4-dien-2-one gave the corresponding Baylis-Hillman adducts in moderate yields in DMSO under the catalysis of DBU or PMe3, respectively. Moderate diastereoselectivities were observed in the reaction of 3-benzylpenta-3,4-dien-2-one with N-arylmethylidene-1-naphthalenesulfonamides catalyzed by chiral catalyst cinchona alkaloid derivative TQO {4-（3-ethyl-4-oxa-1-azatricyclo[4.4.0.0^3,8]dec-5-yl）quinolin-6-ol}.