New Releases by William Nack

Saturated N-heterocycles are useful motifs in medicinal chemistry, but their application often hinges on limited synthetic methods. We have developed a strategy for the synthesis of the N-heterocycle 1,2,3,4-tetrahydroquinoline (THQ) using Pd-catalyzed CH functionalization reactions. Beginning from an alkyl picolinamide, a picolinic acid (PA)-directed, Pd-catalyzed sp3 CH arylation reaction yields a 3-arylpropylpicolinamide intermediate. This intermediate is then cyclized via a sequence of ortho sp2 CH iodination followed by CN cross coupling. We explored two methods for this critical iodination: a directed electrophilic aromatic substitution (EAS) method, and a Pd-catalyzed CH iodination reaction. To demonstrate the scope of this strategy, a variety of substituted THQ scaffolds were synthesized, including (+)-angustureine. Finally, a mechanistic hypothesis for the directed EAS reaction is presented, integrating results from the recent literature with our own preliminary mechanistic studies.In the second chapter, a room temperature diastereoselective Pd-catalyzed CH arylation reaction of 8-aminoquinoline (AQ) coupled cycloalkane carboxylic acids is described. Pd-catalyzed bidentate-auxiliary directed CH arylation has been applied extensively for the synthesis of aryl cycloalkane moieties of natural products. We developed an improved room temperature protocol for cycloalkane CH arylation and explored its scope. Further CH functionalization reactions of the arylated products have been examined, and a mechanistic hypothesis is put forth which rationalizes the diastereoselectivity of the reaction, as well as observed reactivity trends.

The remarkable true story of one of America’s finest racehorses.

Documents the rise and tragic fall of 1970s filly racer Ruffian, whose match against Kentucky Derby winner Foolish Pleasure resulted in a life-ending foreleg break, in an account that also traces the author''s love for the sport.

Collected for the first time, the remarkable profiles and investigative stories of William Nack, esteemed Sports Illustrated writer and author of Secretariat: The Making of a Champion.