Chiral synthesis

Quaternary stereocenters: challenges and solutions for organic synthesis
Jens Christoffers and Angelika Baro 
Weinheim, Germany: Wiley-VCH | 2005 | 359 pp | ?100 (HB) | ISBN 3527311076
Reviewed by Laurence Harwood

If ever an aspect of organic synthesis has called out for a book to be written, the area of construction of quaternary stereocentres would drown out all others with its cries. As Steven Ley writes in his foreword, failure to address construction of quaternary centres early in a synthesis ’can lead later to disaster’. Where did all those model studies to construct the [5.3.1]bicycloundecane system of taxol go? They are mostly consigned to obscurity because they did not address those apparently innocuous little gem-dimethyl groups. Well, better late than never, this monograph has appeared and put right an oversight in a most emphatic and informative way.  

The book consists of 12 relatively short chapters and covers a wide range of chemistry without trying to be exhaustive in any area. That is not to say that the subject areas are treated shallowly; rather the contributors have selected fascinating titbits to provide an informative series of overviews. The first two chapters deal with natural product and pharmaceutical targets and the remainder deal with reaction types, covering the aldol reaction, Michael additions, rearrangements, cycloadditions, asymmetric Heck reaction, ketone alkylations, asymmetric allylic alkylations and radical reactions as well as applications of phase transfer catalysis and enzymes.  

This is a handsome little book and, as well as being destined for the shelves of all institutional libraries, I expect it to become a must for anyone who has any pretensions to the practice of organic synthesis.