Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2019 Mar 11;58(11):3361-3367.
doi: 10.1002/anie.201809511. Epub 2019 Feb 7.

Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts

Anil K Gupta  1 , Xiaopeng Yin  1 , Munmun Mukherjee  1 , Aman A Desai  1 , Aliakbar Mohammadlou  1 , Kelsee Jurewicz  1 , William D Wulff  1
Affiliations

Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts

Anil K Gupta et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: aldehydes; asymmetric catalysis; borate esters; epoxides; ligand designs.

PubMed Disclaimer

Publication types

LinkOut - more resources