Organic Reactions, Volume 73: Allylboration of Carbonyl Compounds

Allylic boron compounds have gained a prominent position as atruly practical class of synthetic reagents in the past twenty–fiveyears. Their main application as a method for the stereoselectivesynthesis of homoallylic alcohols by allyl–transfer to carbonylcompounds is essentially unmatched. In this process, a newcarbon–carbon bond is formed, and up to two new stereogenic centersare created in a predictably controlled manner. Highly effectiveand general enantioselective variants are available, with countlessapplications in the total syntheses of polyacetate andpolypropionate natural products. Furthermore, the residual allylicunit can be manipulated through a number of differenttransformations such as oxidative cleavage, olefin metathesis,hydrometalations, and many others. The discovery of Lewis andBrønsted acid catalyzed manifolds recently, has opened newdoors for further development of this important reaction. This bookprovides an up–to–date, comprehensive survey of the literature ofthis rich chemistry as it pertains to organic synthesis.

Consistent with the goal of Organic Reactions, thecontent and presentation emphasize the preparative aspects of thereactions, giving considerable attention to the scope andlimitations of the individual transformations along with detailedexperimental procedures. A tabular survey of all examples ofcarbonyl allylboration used in organic synthesis is presented innine tables organized by type of allylic boron reagent withlistings within each table according to increasing carbon number ofthe carbonyl substrates.

The literature is covered through December 2010, including a newlisting of nearly 200 literature citations that supplement theoriginal coverage of 834 references used in the earlier hard coverversion of the chapter. Allylboration of Carbonyl Compoundsis intended to be a useful, easily read reference book for allpractitioners of synthetic organic chemistry working in academicand industrial laboratories.

PREFACE  ix

ALLYLBORATION OF CARBONYL COMPOUNDS
Dennis G. Hall and Hugo Lachance 1

INDEX  581

DENNIS G. HALL received his PhD from Université deSherbrooke in 1995 and is now University Professor of Chemistry atthe University of Alberta, Canada. The unifying theme of hisresearch program is the development of new synthetic and biologicalapplications of organoboronic acid derivatives, with topicsincluding stereocontrolled reaction methodology, catalysis,multicomponent reactions, and chemical biology.

HUGO LACHANCE received his PhD from the University ofAlberta in 2006 under the supervision of Prof. Dennis Hall. He isnow Scientific Coordinator at Pharmaqam and Adjunct Professor atUniversité du Québec à Montréal. His researchinterests include asymmetric methodology, bioactive naturalproducts, biological target identification, and proteinlabeling.