Issue 9, 2014

LDA-promoted asymmetric synthesis of β-trifluoromethyl-β-amino indanone derivatives with virtually complete stereochemical outcome

Abstract

We demonstrate that reactions between various 1-indanones and (SS)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine, conducted in the presence of catalytic amounts of LDA, occur with virtually complete stereochemical outcome, offering reliable and generalized access to biologically relevant β-trifluoromethyl-β-amino indanone derivatives. The products can be isolated in diastereomerically pure form simply by washing the crude reaction mixture with hexanes, underscoring practicality of the present method.

Graphical abstract: LDA-promoted asymmetric synthesis of β-trifluoromethyl-β-amino indanone derivatives with virtually complete stereochemical outcome

Supplementary files

Article information

Article type
Paper
Submitted
12 Mph 2013
Accepted
25 Pun 2013
First published
25 Pun 2013

RSC Adv., 2014,4, 4763-4768

LDA-promoted asymmetric synthesis of β-trifluoromethyl-β-amino indanone derivatives with virtually complete stereochemical outcome

C. Xie, H. Mei, L. Wu, V. A. Soloshonok, J. Han and Y. Pan, RSC Adv., 2014, 4, 4763 DOI: 10.1039/C3RA45773G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements