Hydrocyanation summary

Before discussing hydrocyanation chemistry we will explore the interaction of zero-valent nickel phosphite complexes with various independent components of the catalytic system. Then, in turn, we will examine the catalyzed addition of HCN to butadiene, the isomerization of olefins, and the addition of HCN to monoolefins. Finally, a summary of the mechanism as it is now understood will be presented. 

A graphical summary of the developed organocatalytic hydrocyanation methods and comparison of their main key features are given in Scheme 5.11. 

Over the past half-dozen years, many laboratories have focused their efforts on the development of chiral hydrogen bond donors that function as catalysts for enantioselective organic reactions. One of the earliest successes in this area came from Jacobsen and co-workers, who reported the use of peptide-like chiral urea-based catalysts for the hydrocyanation of aldimines and ketoimines [40, 41]. Several other laboratories have also reported highly enantioselective transformations catalyzed by a chiral hydrogen bond donor. The following sections provide a summary of the many developments in hydrogen bond-catalyzed enantioselective reactions, along with a discussion of mechanisms and selectivity models. 

Macy, R. (1937). Hydrocyanic acid Its military history and a summary of its properties (Edgewood Arsenal Tech. Rep. No. 219). Edgewood Arsenal, MD War Department, Chemical Warfare Service. (DTIC No. AD-B957 032)... 

Rudolph Macy, Hydrocyanic Acid Its Military History and a Summary of its Properties. EATR 219, 20 May 37. 

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