Recent Developments in the Reformatsky-Claisen Rearrangement 英文参考文献.docVIP

Molecules 2012, 17, 14249-14259; doi:10.3390/molecules171214249 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Recent Developments in the Reformatsky-Claisen Rearrangement Jun Ishihara * and Susumi Hatakeyama Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan; E-Mail: susumi@nagasaki-u.ac.jp * Author to whom correspondence should be addressed; E-Mail: jishi@nagasaki-u.ac.jp; Tel.: +81-95-819-2427; Fax: +81-95-819-2426. Received: 8 November 2012; in revised form: 21 November 2012 / Accepted: 27 November 2012 / Published: 30 November 2012 Abstract: The rearrangement of allyl ?-bromoacetates with Zn dust is known as the Reformatsky-Claisen rearrangement. Whereas the Ireland-Claisen rearrangement has been widely used in the synthesis of a diverse range of natural products, the Zn-mediated Reformatsky-Claisen rearrangement has not been utilized so often. In this article, we will provide an overview of recent advances in the Reformatsky-Claisen rearrangement field, including the In-mediated Reformatsky-Claisen rearrangement we have recently developed. Keywords: Reformatsky-Claisen rearrangement; Reformatsky reaction; Claisen rearrangement; zinc; indium 1. Introduction The development of new methods for stereoselective carbon-carbon bond formation has been important in the creation of useful molecules such as drugs and other chemical entities. [3,3]-Sigmatropic rearrangements are reliable reactions for selective carbon-carbon bond formation, in particular, the Claisen rearrangement is one of the most competent methods to provide useful building blocks for the synthesis of natural products [1–4]. The synthetic utility of this reaction has prompted the development of a considerable number of variants of the classical Claisen rearrangement [5–9]. For instance, zinc-mediated [3,3]-sigmatropic rearrangement of ?-haloest