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 Okt. 2013
Accepted
25 Nov. 2013
First published
25 Nov. 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

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