Asymmetric Organocatalysis: From Infancy to Adolescence

After an initial period of validating asymmetric organocatalysis by using a wide range of important model reactions that constitute the essential tools of organic synthesis, the time has now been reached when organocatalysis can be used to address specific issues and solve pending problems of stereochemical relevance. This Review deals with selected studies reported in 2006 and the first half of 2007, and is intended to highlight four main aspects that may be taken as testimony of the present status and prospective of organocatalysis: a) chemical efficiency; b) discovery of new substrate combinations to give new asymmetric syntheses; c) development of new catalysts for specific purposes by using mechanistic findings; and d) applications of organocatalytic reactions in the asymmetric total synthesis of target natural products and known compounds of biological and pharmaceutical relevance. As Bernini's David, in the prime of adolescence, fought Goliath armed only with a sling and a stone, organocatalysis uses simple organic molecules to address some fundamental issues of organic synthesis. Important questions concern the chemical efficiency of such processes and the development of viable and simple routes to natural products and drug candidates.