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在铑催化反应中使用 C(2)-对称手性双亚砜配体:四芳基硼酸钠对色烯酮的不对称 1,4-加成。

A C(2)-symmetric chiral bis-sulfoxide ligand in a rhodium-catalyzed reaction: asymmetric 1,4-addition of sodium tetraarylborates to chromenones.

机构信息

National Engineering Research Center of Chiral Drugs and Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

出版信息

J Am Chem Soc. 2010 Apr 7;132(13):4552-3. doi: 10.1021/ja1005477.

DOI:10.1021/ja1005477
PMID:20353203
Abstract

A new C(2)-symmetric chiral bis-sulfoxide ligand, (R,R)-1,2-bis(tert-butylsulfinyl)benzene, has been designed and prepared by the reaction of (R)-benzyl tert-butylsulfoxide with (R)-thiosulfinate. This ligand exhibits excellent enantioselectivities in the Rh-catalyzed asymmetric 1,4-addition reaction. In particular, the present work has realized access to optically pure flavanones for the first time through 1,4-addition of arylboronic reagents to chromenones.

摘要

一种新的 C(2)对称手性双砜配体,(R,R)-1,2-双(叔丁基亚砜基)苯,通过(R)-苄基叔丁基亚砜与(R)-硫代亚磺酸钠的反应设计和制备。该配体在 Rh 催化的不对称 1,4-加成反应中表现出优异的对映选择性。特别是,本工作首次通过芳基硼酸试剂对色烯酮的 1,4-加成反应实现了手性纯黄烷酮的获得。

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