两种源自VANOL的手性硼酸酯催化剂用于醛的催化不对称环氧化反应
Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts.
作者信息
Gupta Anil K, Yin Xiaopeng, Mukherjee Munmun, Desai Aman A, Mohammadlou Aliakbar, Jurewicz Kelsee, Wulff William D
机构信息
Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
出版信息
Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3361-3367. doi: 10.1002/anie.201809511. Epub 2019 Feb 7.
A highly diastereo- and enantioselective method for the epoxidation of aldehydes with α-diazoacetamides has been developed with two different borate ester catalysts of VANOL. Both catalytic systems are general for aromatic, aliphatic, and acetylenic aldehydes, giving high yields and inductions for nearly all cases. One borate ester catalyst has two molecules of VANOL and the other only one VANOL. Catalysts generated from BINOL and VAPOL are ineffective catalysts. An application is shown for access to the side-chain of taxol.
已开发出一种使用两种不同的VANOL硼酸酯催化剂，通过α-重氮乙酰胺对醛进行环氧化的高非对映和对映选择性方法。两种催化体系对芳香醛、脂肪醛和炔醛均适用，几乎在所有情况下都能给出高收率和高对映体过量值。一种硼酸酯催化剂含有两个VANOL分子，另一种仅含有一个VANOL分子。由BINOL和VAPOL生成的催化剂是无效催化剂。展示了其在紫杉醇侧链合成中的应用。
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