Synthesis of Natural Products By Rhodium-Mediated Intramolecular C-H Insertion

Taber, Douglass F.; Stiriba, Salah‐Eddine

doi:10.1002/(sici)1521-3765(19980615)4:6<990::aid-chem990>3.0.co;2-u

Cited by 64 publications

(27 citation statements)

References 9 publications

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“…This field has seen an immense resurgence in the past decade, but it is important to recall its illustrious history dating back to the very origins of organic chemistry. While the potential benefit of manipulating a seemingly inert C-H bond has been frequently reviewed and discussed in recent years, [1][2][3][4][5][6][7][8] the philosophical precepts and implications were clearly articulated by visionaries such as Barton and Breslow several decades ago. 9,10 In this critical review, a historical collection of syntheses that highlight the strategic advantage of C-H functionalization have been selected to further exemplify these benefits.…”

Section: Introduction ''C-h Activation Is At the Center Of Organic Ch...mentioning

confidence: 99%

C–H functionalization logic in total synthesis

2011

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In this critical review, the strategic and economic benefits of C-H functionalization logic will be analyzed through the critical lens of total synthesis. In order to illustrate the dramatically simplifying effects this type of logic can potentially have on synthetic planning, we take the reader through a series of case studies in which it has already been successfully applied. In the first section, a chronological look at key historical syntheses will be examined, leading into modern day examples. In the second section, our own experience with applying and executing synthesis with a C-H functionalization "mindset" will be discussed (114 references).

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Section: Introduction ''C-h Activation Is At the Center Of Organic Ch...mentioning

confidence: 99%

C–H functionalization logic in total synthesis

2011

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“… 6 – 10 Regio-, 11 diastereo-, 12 and enantioselective 13 – 15 variants of this reaction have been developed, demonstrating the utility of Rh-based catalysts in accessing a large region of chemical space. 7 , 16 Though Rh-catalyzed C–H insertion reactions have been used extensively in synthesis, there have been a relatively small number of computational studies on mechanisms and the origins of regio- and stereoselectivity for these reactions. 17 – 20 In particular, computational studies focusing on reactions of α-diazocarbonyl compounds have been limited, despite the extensive use of these substrates for intramolecular C–H insertion reactions to afford cyclic esters and ketones ( e.g.…”

Section: Introductionmentioning

confidence: 99%

Cryptic post-transition state bifurcations that reduce the efficiency of lactone-forming Rh-carbenoid C–H insertions

Hare

Tantillo

2017

Chem. Sci.

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“…Although impressive progress in the area of activation of C-H bonds has been made recently, 7 the direct functionalization is still limited to sp 2 C-H bonds and activated sp 3 C-H bonds. Unactivated alkane C-H bonds remain resistant to direct functionalization, 8 particularly in the context of dendrimers. To use thiophene dendrons with alkyl chains as synthetic building blocks, the main methodology available is to functionalize the focal point (the only a position left in thiophene dendrons) and then attach to a core or self-couple.…”

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confidence: 99%