Highly diastereoselective synthesis of spiro[tetrahydrothiophene-3,3-pyrazol] with an all-carbon quaternary stereocenter via [3+2] cascade Michael/Michael cyclization catalyzed by DABCO

被引：7

作者：

Cai, Guowei ^{[1
]}

Liu, Shuang ^{[1
]}

Zhang, Jiayong ^{[1
]}

Ren, Yuanyuan ^{[1
]}

Wang, He ^{[1
]}

Miao, Zhiwei ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 09期

基金：

中国国家自然科学基金;

关键词：

Cascade Michael; Michael cyclization; DABCO; diastereoselective synthesis; spiro[tetrahydrothiophene-3; 3-pyrazol; PYRAZOLONE DERIVATIVES; SPIROOXINDOLES; ANNULATION; OXINDOLES; SYSTEMS;

D O I：

10.1080/00397911.2016.1174780

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective formation of spiro[tetrahydro thiophene-3,3-pyrazol] derivatives has been achieved via a Michael/Michael cyclization reaction. The reaction was performed using trans-ethyl 4-mercapto-2-butenoate 1 with various 4-benzylidene-5-methyl-2-phenylpyrazolones 2 catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) in toluene at 0 degrees C. The reaction proceeds rapidly and affords the corresponding spiro[tetrahydrothiophene-3,3-pyrazol] derivatives in excellent yields and moderate to excellent diastereoselectivities (up to 98% yield and >20:1 dr).

引用

页码：793 / 798

页数：6

共 28 条

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