Erratum: (S)-2-[(R)-Fluoro(phenyl)methyl]oxirane: A general reagent for determining the ee of α-chiral amines (Organic Letters (2005) 7 (3829-3832))

Full text of DOI:10.1021/ol1008735

ORGANIC
LETTERS
2010
Vol. 12, No. 13
3116
Additions and Corrections
Volume 7, 2005
Sergi Rodr´ıguez-Escrich, Dana Popa, Ciril Jimeno,
Anton Vidal-Ferran,* and Miquel A. Perica`s*
(S)-2-[(R)-Fluoro(phenyl)methyl]oxirane: A General Reagent for
Determining the ee of R-Chiral Amines.
Pages 3829-3832. It has recently been established unambigu-
ously1 that the stereospecific ring-opening fluorination of
[(2S,3S)-3-phenyloxiran-2-yl]methyl p-toluenesulfonate, previ-
ously identified as proceeding with inversion,2 takes place with
retention of configuration.
Accordingly, the configuration at C-3 in structures 1, 3, and 5
in this publication must be changed from R to S. The title should
refer to (S)-2-[(S)-fluoro(phenyl)methyl]oxirane, and Schemes
1 and 2 should be replaced by the following ones.
Scheme 1
Scheme 2
None of the conclusions of the original publication are modified
by this stereochemical correction.
We thank Prof. Stephen G. Davies for thorough exchange of
information prior to publication of his results.
(1) Cresswell, A. J.; Davies, S. G.; Lee, J. A.; Roberts, P. M.; Thomson,
J. E.; Tyte, M. J. Org. Lett. 2010, 12, DOI: 10.1021/ol051110j
(2) Islas-Gonza´lez, G.; Puigjaner, C.; Vidal-Ferran, A.; Moyano, A.; Riera,
A.; Perica`s, M. A. Tetrahedron Lett. 2004, 45, 6337–6341.
OL1008735
10.1021/ol1008735
Published on Web 05/28/2010