Tin in Organic Synthesis

Among a variety of organotin compounds, allylstannanes, in conjunction with activation of the carbonyl substrates by means of a Lewis acid, are known to be reactive enough for a wide range of synthetic applications. Because excellent and extensive review articles are already available [1], only progress made after publication of these articles is discussed in this chapter (Section 12.2). 

When vinyl- or a-alkoxyalkyltin compounds are exposed to alkyllithium, unique hn-hfhium exchange occurs, conveniently generating organolithium species that are otherwise difficult to obtain. Although it is a long time since the discovery of these procedures by Seyferth [2] and ShU [3], respechvely, their usefulness has never faded. Recent apphcahons will be covered in Sechon 12.3. 

Sechon 12.4 also deals with transmetalation, in which a metal-carbon bond is transferred from tin to palladium 11). The organic residues moved on the palladium are coupled with a variety of electrophiles. This reaction, which was first discovered by Migita-Kosugi [4] and later developed by Stille [5], is now recognized as one of the most useful methods for cross-couphng. 

Radical chemistry has experienced a renaissance over fhe last two decades. A 

Main Group Metals in Organic Synthesis. Edited by H. Yamamoto, K Oshima Copyright 2004 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim ISBN 3-527-30508-4 

---

M. Pereyre, J.-P. Quintard, and A Rahm, Tin in Organic Synthesis, Butterworths, London, 1987. 

The synthetic applications involving tin-oxygen bonds in organic chemistry (including carbohydrates) have been reviewed in a book on the use of tin in organic synthesis [7]. 

Pereyre M, Quintard J-P, Rahm A (1987) Tin in organic synthesis, Butterworths, London... 

---