Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

Huang, Xiaolei; Nguyen, Minh Hieu; Pu, Maoping; Zhang, Luoqiang; Robin, Yonggui; Wu, Yun‐Dong; Zhou, Jianrong Steve

doi:10.1002/ange.202000859

Cited by 9 publications

(3 citation statements)

References 122 publications

(17 reference statements)

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“…Very recently, Zhou and co‐workers disclosed an enantioselective reductive Heck bicyclization of enynes, which accessed azabicyclo[3.1.0]hexanes with Ph 2 SiH 2 as a hydride donor, Norphos as a chiral ligand, and i‐ PrOH as a solvent (Scheme 56). [ 69 ] The desired products were achieved in excellent yields and ees with good functional group tolerance. A plausible mechanism was suggested.…”

Section: Palladium‐catalyzed Asymmetric Reductive Heck Reactionsmentioning

confidence: 99%

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive‐Heck Reactions

2021

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Heck reaction is one of the most important carbon‐carbon bond forming reactions with wide applications in organic synthesis. Considerable advances of enantioselective Heck reaction have been achieved in the past decades. This review focuses on recent development of catalytic asymmetric Heck reaction and reductive Heck reaction, which covers intermolecular and intramolecular versions since 2011. The article is organized in terms of the catalysts and olefin substrates.

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Section: Palladium‐catalyzed Asymmetric Reductive Heck Reactionsmentioning

confidence: 99%

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive‐Heck Reactions

2021

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“…In 2020, the Zhou group described a novel Pd‐catalyzed asymmetric reduction alkylation of enynes through the Heck strategy, allowing the facile generation of optically active 5/3‐bisazacyclic products in generally good yields (Scheme 41). [56] This protocol was carried out in the presence of Pd(dba) 2 (5 mol%), ( S,S )‐Norphos (5 mol%), NaOAc (2.0 equiv.) in isopropanol at 50 °C for 12 h, and a series of chiral [3.1.0]azacycles were obtained in good yields with excellent enantioselectivity.…”

Section: Heck/heck Tandem Reactionmentioning

confidence: 99%

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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“…The chiral ligand‐control approach plays the key role for achieving a high level of asymmetric induction. In 2020, Zhou and co‐workers presented asymemetric Heck bicyclization of enynes to access 3‐azabicyclo[3.1.0]hexanes via intercepting the late‐stage organopalladium species with hydride donors or carbon nucleophiles (Scheme 16a) [53] . When silanes 72 were used as the hydride donors, the optimal conditions were established as 5 mol % of Pd(dba) 2 along with 5 mol % of Norphos ligand in isopropanol at 50 °C.…”

Section: Transition Metal‐catalyzed Synthesis Of 3‐azabicyclo[310]hex...mentioning

confidence: 99%

Synthesis of 3‐Azabicyclo[3.1.0]hexane Derivates

Feng

Huang

et al. 2023

Chemistry A European J

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hexanes are an important class of nitrogencontaining heterocycles that have been found to be key structural features in a wide range of biologically active natural products, drugs, and agrochemicals. As a cutting-edge area, the synthesis of these derivatives has made spectacular progress in recent decades, with various transition-metal-catalyzed and transition-metal-free catalytic systems being developed. In this review, we provide an overview of recent advances in the efficient methods for the synthesis of 3-azabicyclo[3.1.0]hexane derivatives since 2010, emphasizing the scope of substrates and synthesis' applications, as well as the mechanisms of these reactions.

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Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

Abstract: Asymmetric reductive and alkynylative heck bicyclization of enynes to access conformationally restricted aza[3.1.0]bicycles

Cited by 9 publications

References 122 publications

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive‐Heck Reactions

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive‐Heck Reactions

Transition‐Metal‐Catalyzed Transformations Involving the Heck Reaction

Synthesis of 3‐Azabicyclo[3.1.0]hexane Derivates

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