Switching the Reactivity of Dihydrothiopyran-4-one with Aldehydes by Aqueous Organocatalysis: Baylis-Hillman, Aldol, or Aldol Condensation Reactions

被引：37

作者：

Abaee, M. Saeed ^{[1
]}

Mojtahedi, Mohammad M. ^{[1
]}

Pasha, Ghasem F. ^{[1
]}

Akbarzadeh, Elahe ^{[2
]}

Shockravi, Abbas ^{[2
]}

Mesbah, A. Wahid ^{[1
]}

Massa, Werner ^{[3
]}

机构：

[1] Chem & Chem Engn Res Ctr Iran, Dept Organ Chem, Tehran, Iran

[2] Tarbiat Moallem Univ, Dept Chem, Tehran 1571914911, Iran

[3] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 19期

基金：

美国国家科学基金会;

关键词：

ORGANIC-SYNTHESIS; BASE CATALYST; EFFICIENT; ADDUCTS; ESTERS; WATER; CYCLIZATION; MECHANISM; ENONES;

D O I：

10.1021/ol202145w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An aqueous medium containing catalytic amounts of a tertiary amine was employed to direct the chemoselectivity of the reaction of aldehydes with la. With DBU, 2 was formed at room temperature as a rare exemplary of Baylis-Hillman reactions in heterocyclic enones. DABCO alternated the pathway toward an aldol reaction to form synlanti mixtures of 3 with the syn isomers being the major products. With Et3N, aldol condensation dominated.

引用

页码：5282 / 5285

页数：4

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