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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

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
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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}.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 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).
关键词 Baylis-Hillman reaction diastereoselectivity 3-methylpenta-3 4-dien-2-one 3-benzylpenta-3 4-dien-2-one chiral catalyst TQO Baylis-Hillman reaction, diastereoselectivity, 3-methylpenta-3,4-dien-2-one, 3-benzylpenta-3,4-dien-2-one, chiral catalyst TQO
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