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CHAPTER 1

Asymmetric C–H Bond Insertion Reactions

C–H bond insertion reactions have been recognized and investigated for a long time with a broad range of applications in organic synthesis. Recently, inspiring progress, especially on the dirhodium carbenoids, have been accomplished by an asymmetric approach. This chapter provides a general overview of these impressive advances in three sections, including C–H bond insertion by metal carbenoids, metal nitrenoids, and metal oxo species. Starting with carbene chemistry, the chapter concentrates on an array of chiral dirhodium catalysts, carbene precursors, especially the donor/acceptor ones, which are crucial to the success of highly selective, tunable, and efficient intermolecular asymmetric C–H bond insertion reactions, and relatively mature catalytic systems exemplified vividly by the combined C–H functionalization/Cope rearrangement (CHCR). Moreover, this methodology is further integrated with computational studies providing detailed mechanistic and prediction models. Next, breakthroughs in other metal carbenoids are also discussed, followed by the introduction of C–H bond insertion by metal nitrenoids and metal oxo species. C–H bond insertion reactions have streamlined the construction of C–C, C–N, and C–O bonds in organic synthesis for a long time. In recent years, impressive progress has been accomplished in the asymmetric approach. According to the type of the formed bonds, these inspiring achievements will be introduced in three sections in the first chapter of this book, including C–H bond insertion by metal carbenoids, metal nitrenoids, and metal oxo species.

Print publication date: 13 Aug 2015
Copyright year: 2015
Print ISBN: 978-1-78262-102-7
PDF eISBN: 978-1-78262-196-6
ePub eISBN: 978-1-78262-654-1
Citation:
From the book series:
Catalysis Series