Asymmetric Michael Addition Reaction under the Control of the Evans Chiral Auxiliary (Ⅱ)

doi:10.6023/cjoc1106191

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (01): 160-164.DOI: 10.6023/cjoc1106191 Previous Articles Next Articles

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Evans 手性助剂控制的不对称Michael 加成立体选择性研究(Ⅱ)

樊会丹, 张从海, 严胜骄, 林军

云南大学化学科学与工程学院教育部自然资源药物化学重点实验室昆明 650091

收稿日期:2011-06-19 修回日期:2011-08-02 发布日期:2011-09-26
通讯作者: 林军 E-mail:linjun@ynu.edu.cn
基金资助:
国家自然科学基金(Nos. 30860342, 20762013)和云南省自然科学基金(No. 2009CC017)资助项目.

Asymmetric Michael Addition Reaction under the Control of the Evans Chiral Auxiliary (Ⅱ)

Fan Huidan, Zhang Conghai, Yan Shengjiao, Lin Jun

Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091

Received:2011-06-19 Revised:2011-08-02 Published:2011-09-26
Contact: Lin Jun E-mail:linjun@ynu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 30860342, 20762013) and the Natural Science Foundation of Yunnan Province (No. 2009CC017).

Chiral auxiliaries controlled asymmetric reaction is one of the main methods in asymmetric synthesis. Under the control of the Evans auxiliary and catalyzed by FeCl₃, different Grignard reagents were added asymmetrically to the substrates 1 by the way of 1,4-Michael addition reaction, and a series of Michael addition products 2a～2h which containing two chiral centers have been synthesized with higher stereoselectivity. Among them, compounds 2d and 2e achieved high diastereospecifically up to 98% de. The results showed that the steric hindrance of the Grignard reagents is the main factor which influences the stereoselectivity of Micheal addition.

Key words: asymmetric Michael addition, Evans chiral auxiliary, diastereoselectivity

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Fan Huidan, Zhang Conghai, Yan Shengjiao, Lin Jun . Asymmetric Michael Addition Reaction under the Control of the Evans Chiral Auxiliary (Ⅱ)[J]. Chin. J. Org. Chem., 2012, 32(01): 160-164.

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Evans 手性助剂控制的不对称Michael 加成立体选择性研究(Ⅱ)

Asymmetric Michael Addition Reaction under the Control of the Evans Chiral Auxiliary (Ⅱ)

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