Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters
被引:191
作者:
Chen, Wen-Bing
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Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
Chen, Wen-Bing
[1
,3
]
Wu, Zhi-Jun
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机构:
Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
Wu, Zhi-Jun
[2
]
Hu, Jing
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Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
Hu, Jing
[1
]
Cun, Lin-Feng
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Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
Cun, Lin-Feng
[1
]
Zhang, Xiao-Mei
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Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
Zhang, Xiao-Mei
[1
]
Yuan, Wei-Cheng
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Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
Yuan, Wei-Cheng
[1
]
机构:
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
The first example of a direct catalytic asymmetric intermolecular aldol reaction of 3-isothiocyanato oxindoles to simple ketones with bifunctional thiourea-tertiary amine as catalyst is reported. This strategy provides a promising approach for the asymmetric synthesis of a range of enantioenriched spirocyclic oxindoles bearing two highly congested contiguous tetrasubstituted carbon stereocenters. Versatile transformations of the spirocyclic oxindole products into other structurally diverse spirocyclic oxindoles have also been demonstrated.