Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes
Name
nihms535721.pdf
Size
286.66 KB
Format
Adobe PDF
Checksum (MD5)
596253fa1a617d2cfe2f645edee246bd
Author(s)
Do, Hien-Quang
Chandrashekar, E. R. R.
Fu, Gregory C
Date Issued
October 2013
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Do, Hien-Quang et al. “Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes.” Journal of the American Chemical Society 135, 44 (October 2013): 16288–16291 © 2013 American Chemical Society
Version
Author's final manuscript
Abstract
A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/JA408561B
