Catalyst‐Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron‐Deficient Olefins

Kan, S. B. Jennifer; Maruyama, Haruhiko; Akakura, Matsujiro; Kano, Taichi; Maruoka, Keiji

doi:10.1002/ange.201705546

Cited by 29 publications

(1 citation statement)

References 59 publications

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“…26 27 However, in some cases, hypothesis-driven catalyst redesign has been used to develop stereodivergent transformations. 28 A notable example of the latter approach is the development of a direct and stereodivergent organocatalytic Mannich reaction by the Barbas group. An initial report documented an l -proline ( 2a ) catalyzed Mannich reaction of isovaleraldehyde and N -PMP-protected α-imino ethyl glycolate to generate the syn -amino aldehyde 3 (Scheme 2 ).…”

Section: Mono-catalysismentioning

confidence: 99%

Stereodivergent Carbon–Carbon Bond-Forming Reactions

Healy

2024

Synthesis

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Stereodivergent catalysis has emerged as a compelling strategy for achieving stereochemical diversity in small-molecule library design and natural product synthesis. In this short review, key examples of pioneering catalytic carbon–carbon bond-forming transformations that provide access to all stereoisomers of a given product are presented. Current trends and future directions in the field are discussed, highlighting ongoing initiatives to enhance the efficiency and broaden the scope of stereodivergent methodologies.1 Introduction2 Mono-catalysis2.1 Change of Reaction Conditions2.2 Change of Catalyst3 Multi-catalysis3.1 Bifunctional Catalysis3.2 Sequential/Cascade Catalysis3.3 Synergistic/Cooperative Catalysis4 Conclusions and Outlook

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Section: Mono-catalysismentioning

confidence: 99%

Stereodivergent Carbon–Carbon Bond-Forming Reactions

Healy

2024

Synthesis

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Diastereodivergent Synthesis of Bridged Tetrahydroisoquinoline Derivatives Catalyzed by Modularly Designed Organocatalysts

et al. 2020

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The diastereodivergent synthesis of bridged 1,2,3,4‐tetrahydroisoquinoline derivatives has been achieved by using appropriate modularly designed organocatalysts (MDOs) that are self‐assembled in situ from amino acids and cinchona alkaloid derivatives. The domino Mannich/aza‐Michael/aldol reaction between (E)‐2‐[2‐(3‐aryl‐3‐oxoprop‐1‐en‐1‐yl)phenyl]acetaldehydes and ethyl or benzyl (E)‐2‐[(4‐methoxyphenyl)imino]acetates catalyzed by MDOs gives two different diastereomers of the desired bridged tetrahydroisoquinolines in good yields and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to >99% ee). The diastereodivergence was achieved in the aldol reaction step.

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E/Z Photoisomerization of Olefins as an Emergent Strategy for the Control of Stereodivergence in Catalysis

et al. 2022

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The stereoselective photoisomerization of olefins via Energy Transfer (EnT) sensitization bears significant potential in the context of rational design of catalytic stereodivergent methodologies. Whereas approaches for controlling the access to E‐ and Z‐ isomers depend highly on the nature of the catalyst – and therefore are not easily implemented as a general strategy – EnT catalysis has emerged in recent years as an increasingly powerful tool for olefin geometry control in a nearly perfect step‐economic fashion. Moreover, this approach presents both high functional group tolerance and, most notably, has demonstrated ample multicatalytic compatibility. This feature has enabled the development of tandem stereodivergent catalytic strategies, which are the focus of this Review.

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Catalyst‐Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron‐Deficient Olefins

Cited by 29 publications

References 59 publications

Stereodivergent Carbon–Carbon Bond-Forming Reactions

Stereodivergent Carbon–Carbon Bond-Forming Reactions

Diastereodivergent Synthesis of Bridged Tetrahydroisoquinoline Derivatives Catalyzed by Modularly Designed Organocatalysts

E/Z Photoisomerization of Olefins as an Emergent Strategy for the Control of Stereodivergence in Catalysis

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