Metal catalyzed allylic alkylation: its development in the Trost laboratories

Trost, Barry M.

doi:10.1016/j.tet.2015.06.044

Cited by 182 publications

(76 citation statements)

References 174 publications

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“…This particular subset has found numerous applications and has been reviewed periodically. 178,179,180,181 As such, a limited number of examples are presented here for illustration and the reader is advised to consult previous reviews dedicated to this topic for more information.…”

Section: Dynamic Kinetic Asymmetric Transformationsmentioning

confidence: 99%

Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations

et al. 2017

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An important subset of asymmetric synthesis is dynamic kinetic resolution, dynamic kinetic asymmetric processes and stereoablative transformations. Initially, only enzymes were known to catalyze dynamic kinetic processes but recently various synthetic catalysts have been developed. This review summarizes major advances in non-enzymatic, transition metal promoted dynamic asymmetric transformations reported between 2005 and 2015.

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Section: Dynamic Kinetic Asymmetric Transformationsmentioning

confidence: 99%

Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations

et al. 2017

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“…We were interested in the selective O-allylation of polyols because the allyl group is among the smallest, yet most versatile, units in chemistry 38 . Among all of the allylic alkylation methods established to date, a well-studied and often utilized one is the Pd-catalyzed Tsuji-Trost reaction 39 . Intriguingly, the allylation of aliphatic alcohols by the Tsuji-Trost reaction is often a slow process (1 + 2 to 3, Fig.…”

Section: Resultsmentioning

confidence: 99%

Site-switchable mono-O-allylation of polyols

et al. 2020

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Site-selective modification of complex molecules allows for rapid accesses to their analogues and derivatives, and, therefore, offers highly valuable opportunities to probe their functions. However, to selectively manipulate one out of many repeatedly occurring functional groups within a substrate represents a grand challenge in chemistry. Yet more demanding is to develop methods in which alterations to the reaction conditions lead to switching of the specific site of reaction. We report herein the development of a Pd/Lewis acid co-catalytic system that achieves not only site-selective, but site-switchable mono-O-allylation of polyols with readily available reagents and catalysts. Through exchanging the Lewis acid additives that recognize specific hydroxyls in a polyol substrate, our system managed to install a versatile allyl group to the target in a site-switchable manner. Our design demonstrates remarkable scope, and is amenable to the direct derivatization of various complex, bioactive natural products.

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“…1a ) 40 – 42 . Regarding the starting materials, those substrates might be preferably prepared through an initial palladium-catalyzed Tsuji-Trost allylation of 2-halophenols, which would provide a more efficient and step-economic way 43 – 45 . Following this initial idea, we investigated the coupling of 2-iodophenol ( 1a ) with 2-phenylallyl acetate ( 2a ) in the presence of PdBr 2 / L1 (Fig.…”

Section: Resultsmentioning

confidence: 99%

The role of allyl ammonium salts in palladium-catalyzed cascade reactions towards the synthesis of spiro-fused heterocycles

Spannenberg

et al. 2020

Nat Commun

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There is a continuous need for designing new and improved synthetic methods aiming at minimizing reaction steps while increasing molecular complexity. In this respect, catalytic, one-pot cascade methodologies constitute an ideal tool for the construction of complex molecules with high chemo-, regio-, and stereoselectivity. Herein, we describe two general and efficient cascade procedures for the synthesis of spiro-fused heterocylces. This transformation combines selective nucleophilic substitution (SN2′), palladium-catalyzed Heck and C–H activation reactions in a cascade manner. The use of allylic ammonium salts and specific Pd catalysts are key to the success of the transformations. The synthetic utility of these methodologies is showcased by the preparation of 48 spiro-fused dihydrobenzofuranes and indolines including a variety of fluorinated derivatives.

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Metal catalyzed allylic alkylation: its development in the Trost laboratories

Cited by 182 publications

References 174 publications

Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations

Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations

Site-switchable mono-O-allylation of polyols

The role of allyl ammonium salts in palladium-catalyzed cascade reactions towards the synthesis of spiro-fused heterocycles

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