2020
DOI: 10.1039/d0cs00769b
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Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications

Abstract: The diversity, utility and mechanistic aspects of asymmetric synthesis with ynamides developed during the last decade is discussed.

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Cited by 170 publications
(34 citation statements)
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“…In this section, recently developed strategies for asymmetric synthesis involving enolonium equivalents as the reaction intermediates will be highlighted. Although asymmetric synthesis involving ynamides has been reviewed recently, [64] we will take a perspective of the enolonium synthon, broadly encompassing activated/unactivated alkynes and amides as substrates and also including photocatalytic conditions.…”
Section: Enantioselective Approach Via Enoloniumsmentioning
confidence: 99%
“…In this section, recently developed strategies for asymmetric synthesis involving enolonium equivalents as the reaction intermediates will be highlighted. Although asymmetric synthesis involving ynamides has been reviewed recently, [64] we will take a perspective of the enolonium synthon, broadly encompassing activated/unactivated alkynes and amides as substrates and also including photocatalytic conditions.…”
Section: Enantioselective Approach Via Enoloniumsmentioning
confidence: 99%
“…In the last 10 years, ynamides, have emerged as very attracting reagents and building blocks for organic synthesis. [1,2] Thanks to their highly polarized triple bond, ynamides have become partners of choice for a myriad of reactions, including cyclizations [3] or asymmetric transformations, [4] through a variety of activation modes. [5][6][7][8][9] In parallel, efficient and robust methods for the synthesis of a broader range of ynamides have been developed.…”
Section: Introductionmentioning
confidence: 99%
“…67 Thus, ynamides display unique reactivities owing to the flexible modulation of EWG and have evolved into versatile synthons and building blocks. [68][69][70][71] We have recently disclosed that ynamides could be used as novel coupling reagents for facilitating amide 72-73 and ester 74-75 bond formation, which were accomplished by taking advantage of the α-addition of carboxylic acid to ynamides (Figure 2a). 71 Furthermore, we have found that the regioselectivity could be reversed by employing basic reaction conditions as exemplified by the regio-and stereoselective hydroamidation 76 and hydrophosphorylation 77 of ynamides.…”
Section: Introductionmentioning
confidence: 99%