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).
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收藏
页码：793 / 798
页数：6
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