By Thomas Wirth, T. Wirth H. Kessler (Editor), K.N. Houk (Editor), J.-M. Lehn (Editor)
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Extra resources for Topics in current chemistry, 208, Organoselenium Chemistry: Modern Developments in Organic Synthesis
Metodologie ed Applicazioni”) and CNR, Rome, is gratefully acknowledged. I thank all collaborators whose names appear in the references for their stimulating enthusiasm and involvement. The technical assistence of Dr. C. Santi in preparing the manuscript is particularly appreciated. 6 References 1. Nicolaou KC, Petasis NA (1984) Selenium in Natural Products Synthesis, CIS, Philadelphia, p 207 2. Paulmier C (1986) Selenium Reagents and Intermediates in Organic Synthesis, Pergamon, Oxford 3. Liotta D (1987) Organoselenium Chemistry, Wiley, New York 4.
78 1 Introduction The chemistry of nucleophilic selenium reagents began in 1973 when Sharpless et al. reported a simple method to prepare a benzeneselenolate equivalent 1 and its usefulness in the nucleophilic ring opening of various epoxides . The subsequent oxidative elimination of the phenylseleno group led to allylic alcohols under mild conditions (Scheme 1). Sodium borohydride (NaBH4) was employed as a reducing reagent to generate 1 from diphenyl diselenide (PhSeSePh) in ethanol.
Unless one of the few commercially available selenenylating agents is employed, the first step consists of the preparation of the appropriate reagent. Next, the reaction with an unsaturated compound, in the presence of an external or an internal nucleophile, affords the addition product which in most cases is not the final product but an intermediate which must be isolated and purified. Often the molecule is subjected to further manipulations that are favored by the presence of the selenium functionality.
Topics in current chemistry, 208, Organoselenium Chemistry: Modern Developments in Organic Synthesis by Thomas Wirth, T. Wirth H. Kessler (Editor), K.N. Houk (Editor), J.-M. Lehn (Editor)