Preparation of Trifluoromethyl Lactol Derivatives via Base Initiated Cyclobutanol Ring Opening to a Laterally Lithiated Trifluoromethyl Ketone

Authors

Daniel Becker, Loyola University ChicagoFollow
Daniel L. Flynn

Document Type

Article

Publication Date

1-1-1996

Publication Title

Synlett

Volume

1996

Issue

1

Pages

57-59

Publisher Name

Georg Thieme Verlag KG

Abstract

Benzocyclobutenone derivatives 4 are converted to the corresponding trifluoromethylcyclobutanols 5 by treatment with trifluoromethyltrimethylsilane in the presence of tetra-n-butylammonium fluoride. These trifluoromethylcyclobutanol derivatives are then treated with LiTMP in the presence of aromatic aldehydes to afford trifluoromethyllactols 6 via a laterally-lithiated trifluoromethylketone intermediate.

Comments

Author Posting © Thieme, 1996. This is the author's version of the work. It is posted here by permission of Thieme for personal use, not for redistribution. The definitive version was published in Synlett, Volume 1996, Issue 1, January 1996. http://dx.doi.org/10.1055/s-1996-5325

Recommended Citation

Becker, Daniel and Flynn, Daniel L.. Preparation of Trifluoromethyl Lactol Derivatives via Base Initiated Cyclobutanol Ring Opening to a Laterally Lithiated Trifluoromethyl Ketone. Synlett, 1996, 1: 57-59, 1996. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1055/s-1996-5325

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Copyright Statement

© 1996 Thieme