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

Guowei CaiState Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, China

Shuang LiuState Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, China

Jiayong ZhangState Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, China

Yuanyuan RenState Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, China

He WangState Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, China

Zhiwei MiaoState Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, ChinaCorrespondence[email protected]

ABSTRACT

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 °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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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

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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

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