Tandem [4 + 2]/[3 + 2] Cycloadditions of Nitroalkenes. 10. trans-2-(1-Methyl-1-phenylethyl)cyclohexanol as a New Auxiliary.

Insofar as one of the fundamenta l object ives of organic synthesis is the const ruct ion of complex molecules from simpler ones, the impor tance of synthet ic efficiency becomes immedia tely apparen t and has been well-recognized.1 The increase in molecula r complexity2 tha t necessar ily accompanies the course of a synthesis provides a guide (and a measure) of synthet ic efficiency. As a goal, one would like to opt imally match the change in molecula r complexity a t each step with react ions of comparable synthet ic complexity. Thus, the crea t ion of many bonds, r ings, and stereocenters in a single t ransfor mat ion is a necessary (though not sufficien t ) condit ion for h igh synthet ic efficiency. The ult imate, perfect match would const itute single-step syntheses. More rea list ica lly, especia lly in view of the desire for general synthet ic methods, the combina t ion of mulScott E. Denmark was born in New York in 1953. He obtained an S.B. degree from MIT in 1975 and carried out research with Daniel Kemp and Richard Holm. His graduate studies at the ETH-Zürich with Albert Eschenmoser culminated with the D. Sc. Tech. degree in 1980. That same year he joined the faculty of the University of Illinois at UrbanasChampaign and was promoted to full professor in 1987. In 1991 he was named the Reynold C. Fuson Professor of Chemistry. His research interests are primarily in the invention of new synthetic reactions, structure and reactivity of organoelement reagents, and the origin of stereocontrol in fundamental carbon-carbon bond forming reactions.