T Ishikawa & S Saito-J. Am. Chem. Soc. 2001

This paper was corrected on September 7, 2001, J. Am. Chem. Soc., 123 (39), 9724 -9724.
Retraction Reason:
We have recently become aware of the presence of two previouus papers by Davies1 very closely related to our work entitled "Novel [2,3]-Sigmatropic Rearrangement for Carbon-Nitrogen Bond Formations" recently published in this journal.2 These two previous papers are clearly indicating that the discovery of [2,3]-sigmatropic rearrangement of this class must be credited to Davies.1 Our insufficient literature search is surely responsible for this serious matter. Therefore, it is appropriate that we should retract our recent paper2 concerned with this chemistry. (1) (a) Davies, S. G.; Jones, S.; Sanz, M. A.; Teixeira, F. C.; Fox, J. F. Chem. Commun. 1998, 2235-2236. (b) Bull, S. D.; Davies, S. G.; Jones, S.; Ouzman, J. V. A.; Price, A. J.; Watkin, D. J. Chem. Commun. 1999, 2079-2080. (2) Ishikawa, T.; Kawakami, M.; Fukui, M.; Yamashita, A.; Urano, J.; Saito, S. J. Am. Chem. Soc. 2001, 123, 7734-7735. Our first manuscript having the same title as this paper covering the content of ref 1a was submitted to this journal on September 21, 1998, whereas Davies submitted his first manuscript (ref 1a) to Chem. Commun. on August 5, 1998. These records are consistent with the idea that Davies and we were independently concerned with the same chemistry at the same time.09/07/2001
Originally Published: J. Am. Chem. Soc. 2001, 123, 7734-7735.
Title: Novel [2,3]-Sigmatropic Rearrangement for Carbon-Nitrogen Bond Formation
Authors: Teruhiko Ishikawa,* Masatomo Kawakami, Miyuki Fukui, Ayako Yamashita, Jin Urano, and Seiki Saito*
Affiliation:
Abstract:
[2,3]-Sigmatropic rearrangement is a widespread method for regiospecific carbon-carbon or carbon-heteroatom bond formation in organic synthesis,1 and enormous examples have been reported including their applications to asymmetric synthesis and natural product synthesis. For aza-versions,2 a number of allylchalcogenide and allylamineimide derivatives have been demonstrated to be usable for transferring amino groups to allylic positions (Scheme 1). However, more simple and efficient methods for the construction of allylic amines from allylic alcohols are desirable.3 And our recent studies on hydroxylamine-based chemistry4 have led us to the discovery of novel [2,3]-sigmatropic rearrangement of O-allylic hydroxylamines in which a negatively charged nitrogen atom is a migration terminus (Scheme 1). In this paper we detail the features of such a [2,3]-sigmatropic rearrangement as a highly useful method for the synthesis of N-hydroxyallylamines, precursors for allylic amines, a biologically important class of compounds.