1532 BOOK REVIEW

Modern Carbonyl Olefination – Methods and Appli- bonyl olefination domino reactions. Low-valent chro- cations; edited by T. Takeda; Wiley-VCH: Weinheim, mium, zinc or titanium mediated olefinations, such as 2004; hard cover, 349 pp, £100.00 / €150.00, ISBN 3- olefinations with the Nysted reagent or Takai-Utimoto 527-30634-X olefinations applying geminal dihaloalkane and chro- mium(II) chloride as reagents, are highlighted by Seijiro Matsubara and Koichiro Oshima in chapter 5. In particu- Carbonyl olefinations inevitably belong to the most lar, the appealing application of the Takai olefination important tools in organic synthesis since they ideally with iodoform to the synthesis of iodoalkenes, that have combine a high degree of convergence with excellent found extensive use in natural product syntheses, nicely chemo- and stereoselectivity. Therefore, it is very surpris- demonstrates the conceptual beauty of metal carbenoid ing that this book is the first endeavor to summarize the reagents in olefination methodology. In chapter 6 (by seemingly different olefination methods and, hence, fill- Michel Ephritikhine and Claude Villiers) the McMurry ing a long existing gap in the bookshelf of synthetic coupling and its related reactions are summarized with a monographs. Here, as the editor Takeshi Takeda clearly dedication of the particular conditions and the breadth of points out in his preface, the marked mechanistic similar- synthetic scope. Interestingly, the McMurry reaction has ities literally demand a common discussion, in particular, reached an increasing level of application in the synthesis since the early days of the Wittig reaction, tremendous of natural and nonnatural products. The development of efforts have been made to refine and establish more and cyclizations that are even catalytic in titanium manifests more selective and specific methodologies for the olefi- the importance and dynamics in the field of organometal- nation of carbonyl compounds. lic reagents and catalysts. Finally, the book closes with a Not surprisingly, the first chapter is intended to the Wittig discussion of asymmetric carbonyl olefinations (by Kiy- reaction (by Michael Edmonds and Andrew Abell), oshi Tanaka, Takumi Furata, and Kaoru Fuji) that have where a historical appreciation to Wittig and Geissler been a logic extension of the Wittig reaction from the opens the concise review on the most important mecha- early days on, in particular, since differentiation of enan- nistic and stereochemical issues and developments of tiotopic carbonyls, dissymmetrization of prochiral carbo- phosphorous ylid and related carbonyl olefinations. Since nyl compounds, and kinetic resolutions of racemic the Wittig and related reactions have already been aldehydes and ketones can be very important strategies in reviewed in the past, this chapter rather displays an intro- complex molecule synthesis. In this final chapter, stereo- ductory character citing the most important references. In chemical, mechanistic and synthetic examples from the chapter 2 (by Naokazu Kano and Takayuki Kawashima), first attempts of asymmetric carbonyl olefination to very Peterson and related reactions are extensively and com- recent strategies are presented and critically discussed. prehensively reviewed, emphasizing stereochemistry and This excellent new book summarizes in a concise fashion reaction mechanisms as well as numerous accesses to α- the current knowledge as well as the major recent devel- silyl carbanions, the crucial starting points for this olefi- opments in a 50-year old, yet rapidly evolving, field. nation reaction. Finally, the germyl, stannyl and plumbyl With many mechanistic, stereochemical and synthetic Peterson reactions are also introduced, thereby demon- examples, the topics are clearly and didactically well pre- strating the vibrant development of this methodology. sented. It addresses graduate students as well as The Julia reaction is broadly presented by Raphaël specialists, both in academia and industry, who are con- Dumeunier and István E. Markó in chapter 3. Mechanis- cerned with carbonyl olefinations in their daily work. tic, stereochemical and synthetic investigations are illus- Therefore, this book deserves a special place on the trated by many instructive examples and applications in bookshelves of synthetic organic chemists. complex molecule synthesis. Metal carbene complexes in carbonyl olefinations are the focus of chapter 4 by Takeshi Takeda and Akira Tsubouchi. Here, the overview Thomas J. J. Müller, Organisch-Chemisches Institut, commences with the well-established Tebbe and related Ruprecht-Karls-Universität Heidelberg. This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. reactions, over the conceptually elegant transformation of E-mail: [email protected] readily available thioacetals to olefins through the inter- mediacy of titanium carbenes, finally to conclude with molybdenum and tungsten carbene olefin metathesis-car-

SYNTHESIS 2004, No. 9, pp 1532–1532 Advanced online publication: 08.06.2004 Art ID: B10904SS © Georg Thieme Verlag Stuttgart · New York