Catalytic Enantioselective Assembly of Homoallylic Alcohols from Dienes, Aryldiazonium Salts, and Aldehydes

An enantioselective multicomponent carbonyl allylation reaction of 1,3-butadienes,a lkynyl bromides and aldehydes hasb eene stablished, leading to the generation of densely functionalized homoallylic alcohols in high levels of structural diversity ands tereoselectivity.T he multicomponent process sequentially comprises the oxidative addition, salt metathesis,i nsertion/p-allyl-Pd formation, asymmetric allylic borylation, ande nantioslecitve carbonyl allylborylation,w herein the alkynyl palladium phosphate in situ generated from the chiral silver phosphatea nd the alkynyl palladium bromide turns out to be ak ey intermediate that allowst he efficient stereochemical control.

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An Enantioselective Multicomponent Carbonyl Allylation of Aldehydes with Dienes and Alkynyl Bromides Enabled by Chiral Palladium Phosphate

Shen

Wang

Tao

et al. 2017

Adv Synth Catal

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Kinetic Resolution of 2‐N‐Acylamido Tertiary Allylic Alcohols: Asymmetric Synthesis of Oxazolines

et al. 2020

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A series of cyclohexyl‐fused SPINOL‐derived phosphoric acids (Cy‐SPA) have been developed to catalyze the kinetic resolution of 2‐N‐acylamido tertiary allylic alcohols, providing access to chiral oxazolines bearing C‐2 alkyl substituents with high enantioselectivities (with s‐factors up to 153). Gram‐scale reaction with 1 mol% catalyst loading and transformations of the chiral products demonstrates the value of these methods.

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Transition‐Metal‐Catalyzed Transformations Involving the Heck Reaction

2023

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Elaborated molecular architectures including complex carbocycles, heterocycles, and polycyclic molecular structures represent an important class of organic compounds because they are ubiquitous structural units in a broad variety of biologically and pharmacologically relevant natural products, medicinal molecules, and functional materials. A major challenge in modern synthetic methodology is the development of strategically efficient and selective construction of these compounds from readily available starting materials. Transition‐metal‐catalyzed transformations involving Heck reaction as the pivotal step have afforded a powerful approach for accessing sophisticated polycyclic skeletons from a set of easy‐to handle starting materials, thus highlighting its potential significance in streamlining the drug discovery process. Over the past few decades, significant effort has been devoted to accessing complex polycyclic derivatives in efficient and versatile routes, and a number of powerful and direct synthetic strategies have been reported. In this review, the latest advances in transition‐metal‐catalyzed transformations involving Heck reaction as the critical step are summarized, which could be divided into six categories: 1) Heck/Sonogashira tandem reaction; 2) Heck/Suzuki tandem reaction; 3) Heck/Heck tandem reaction; 4) Heck/Hiyama tandem reaction; 5) Heck/Cacchi tandem reaction; 6) Heck/C−H bond functionalization tandem reaction.

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Catalytic Enantioselective Assembly of Homoallylic Alcohols from Dienes, Aryldiazonium Salts, and Aldehydes

Cited by 17 publications

References 74 publications

An Enantioselective Multicomponent Carbonyl Allylation of Aldehydes with Dienes and Alkynyl Bromides Enabled by Chiral Palladium Phosphate

An Enantioselective Multicomponent Carbonyl Allylation of Aldehydes with Dienes and Alkynyl Bromides Enabled by Chiral Palladium Phosphate

Kinetic Resolution of 2‐N‐Acylamido Tertiary Allylic Alcohols: Asymmetric Synthesis of Oxazolines

Transition‐Metal‐Catalyzed Transformations Involving the Heck Reaction

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