Decarboxylative 1,2-rearrangement of cyclic carbonates promoted by Lewis acid

Dokai, Yoichi; Saito, Kodai; Yamada, Tohru

doi:10.1039/d2cc03024a

Cited by 2 publications

(2 citation statements)

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“…Finally, the Naproxen-derived 1,2-diol product ( 86 , > 20:1 dr) was successfully converted into its epoxide derivative ( 87 ) via treatment with tri- n -butyl phosphine and diisopropyl azodicarboxylate (DIAD) in CH 2 Cl 2 at ambient temperature, achieving a 76% yield while maintaining a diastereoselectivity of >20:1 (Figure B) . Alternatively, upon reaction with triphosgene in the presence of pyridine in CH 2 Cl 2 , a 1,3-dioxolan-2-one derivative ( 88 ) was synthesized in a 91% yield and with a remarkable diastereoselectivity of >20:1 …”

Section: Results and Discussionmentioning

confidence: 99%

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Asymmetric Cross-Coupling of Aldehydes with Diverse Carbonyl or Iminyl Compounds by Photoredox-Mediated Cobalt Catalysis

Chi,

Liao,

Cheng

et al. 2024

J. Am. Chem. Soc.

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The asymmetric cross-coupling of unsaturated bonds, hampered by their comparable polarity and reactivity, as well as the scarcity of efficient catalytic systems capable of diastereo-and enantiocontrol, presents a significant hurdle in organic synthesis. In this study, we introduce a highly adaptable photochemical cobalt catalysis framework that facilitates chemoand stereoselective reductive cross-couplings between common aldehydes with a broad array of carbonyl and iminyl compounds, including N-acylhydrazones, aryl ketones, aldehydes, and α-keto esters. Our methodology hinges on a synergistic mechanism driven by photoredox-induced single-electron reduction and subsequent radical−radical coupling, all precisely guided by a chiral cobalt catalyst. Various optically enriched β-amino alcohols and unsymmetrical 1,2-diol derivatives (80 examples) have been synthesized with good yields (up to 90% yield) and high stereoselectivities (up to >20:1 dr, 99% ee). Of particular note, this approach accomplishes unattainable photochemical asymmetric transformations of aldehydes with disparate carbonyl partners without reliance on any external photosensitizer, thereby further emphasizing its versatility and cost-efficiency.

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Section: Results and Discussionmentioning

confidence: 99%

“…26 Alternatively, upon reaction with triphosgene in the presence of pyridine in CH 2 Cl 2 , a 1,3dioxolan-2-one derivative (88) was synthesized in a 91% yield and with a remarkable diastereoselectivity of >20:1. 27…”

Section: ■ Introductionmentioning

confidence: 99%