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New Releases by William Nack

William Nack is the author of N-Heterocycle Synthesis Via Bidentate-Auxiliary Directed Remote C-H Functionalization (2016), Ruffian (2007), My Turf (2004), Secretariat (1989) and Big Red of Meadow Stable (1975).

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N-Heterocycle Synthesis Via Bidentate-Auxiliary Directed Remote C-H Functionalization

release date: Jan 01, 2016
N-Heterocycle Synthesis Via Bidentate-Auxiliary Directed Remote C-H Functionalization
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.

Ruffian

release date: May 08, 2007
Ruffian
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.

My Turf

release date: Jan 08, 2004
My Turf
William Nack has won the prestigious Eclipse Award-given annually for the best magazine piece on horseracing-an unprecedented six times. His only previous book, Secretariat: The Making of a Champion, has been eloquently described by Laura Hillenbrand, author of Seabiscuit, as the "gold standard" of horse books.Now, Nack''s finest turf writing, coupled with an ample assortment of dead-on profiles and investigative stories across the world of sports, is brought together in My Turf. Nack serves up unforgettable portraits: from his celebrated account of the death of Secretariat to his homage to both Yankee Stadium and Saratoga, including one-of-a-kind profiles of boxers Sonny Liston and Rocky Marciano, jockeys Willie Shoemaker and Robbie Davis, baseball players Keith Hernandez and the schizophrenic Martin Bergen, basketball coach Rick Pitino, and the chess master Bobby Fischer.

Secretariat

release date: Nov 01, 1989
Secretariat
"Secretariat is an elegantly crafted, exhilarating tale of speed and power, grace and greatness, told with such immediacy that the reader is lost in the rush of horses and the clatter and ring of the grandstand."Laura Hillenbrand, author of Seabiscuit
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