Author : Nai-Wen Tseng
Release : 2009
Genre :
Kind : eBook
Book Rating : 197/5 ( reviews)

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Book Synopsis Transition Metal-catalyzed Carbon-carbon/carbon-heteroatom Bond Formation Reactions Utilizing Strained Ring Systems by : Nai-Wen Tseng

Download or read book Transition Metal-catalyzed Carbon-carbon/carbon-heteroatom Bond Formation Reactions Utilizing Strained Ring Systems written by Nai-Wen Tseng. This book was released on 2009. Available in PDF, EPUB and Kindle. Book excerpt: This thesis focuses on the development of carbon-carbon/carbon-heteroatom bond forming reactions using strained ring systems under transition metal catalysis. The first chapter describes the use of bifunctional organoboron reagents with a rhodium catalyst to synthesize carbocycles through a cascade sequence. The reaction of norbornene derivatives gives vinylcyclopropane and cyclopentene products in moderate to good yield. The mechanistic proposal and insights into the reaction mechanism are presented. Preliminary results from studies toward an enantioselective sequential addition/cyclization process are described. The methodology is subsequently applied in the synthesis of a variety of polycyclic heteroaromatics using bifunctional heteroaryl boronate esters. The second chapter describes studies toward the formation of carbon-heteroatom bonds using cyclopropane derivatives. Under a recently developed Pd(OAc) 2/PhI(OAc)2 catalytic system, methylenecyclopropanes are isomerized to substituted pyridines via a sequential fragmentation/cyclization process. Under same reaction conditions, allylic acetate products are obtained from the isomerization of cyclopropanes through a similar process.