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  

作　　者：施敏 郭英文 李红斌 

机构地区：[1]tate Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China [2]School of Environmental and Chemical Engineering, Shanghai University, Shanghai 201800, China

出　　处：《Chinese Journal of Chemistry》2007年第6期828-835,共8页中国化学（英文版）

基　　金：Project supported by State Key Project of Basic Research （Project 973） （No. G2000048007）, Shanghai Municipal Committee of Science and Technology （Nos. 04JC14083, 06XD14005）, and the National Natural Science Foundation of China （Nos. 20472096, 203900502, and 20672127）.

摘　　要：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}.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}.

关 键 词：Baylis-Hillman reaction diastereoselectivity 3-methylpenta-3 4-dien-2-one 3-benzylpenta-3 4-dien-2-one chiral catalyst TQO 

分 类 号：O625.41[理学—有机化学]