Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins.

Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins.
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设计新型手性酮催化剂。

DOI:
10.1021/jo010838k
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发表时间:
2002
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Shi,Yian
Shi,Yian
中科院分区:
--
文献类型:
--
作者:
Tian,Hongqi;She,Xuegong;Yu,Hongwu;Shu,Lianhe;Shi,Yian

文献摘要

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本文描述了一类新型手性恶唑烷酮酮催化剂,用于不对称环氧化反应。许多环状和无环顺式烯烃已获得高 ee 值。环氧化是立体定向的,在无环体系的环氧化中没有观察到异构化。许多末端烯烃也获得了令人鼓舞的高ee值。机理研究表明电子相互作用在立体分化中发挥重要作用。
This paper describes a new class of chiral oxazolidinone ketone catalyst for asymmetric epoxidation. High ee values have been obtained for a number of cyclic and acycliccis-olefins. The epoxidation was stereospecific with no isomerization observed in the epoxidation of acyclic systems. Encouragingly high ee values have also been obtained for a number of terminal olefins. Mechanistic studies show that electronic interactions play an important role in stereodifferentiation.