Crystallization-Induced Diastereomer Transformation of α-Bromo α′-Sulfinyl Ketones. Diastereodivergent Synthesis of (+)-α-Conhydrine and (−)-β-Conhydrine - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2021

Crystallization-Induced Diastereomer Transformation of α-Bromo α′-Sulfinyl Ketones. Diastereodivergent Synthesis of (+)-α-Conhydrine and (−)-β-Conhydrine

Résumé

Crystallization-Induced Diastereomer Transformation (CIDT) of α-bromo-α'-(R)-sulfinylketones is reported. This process provides not readily accessible enantiopure stereolabile α-bromoketones, which after diastereoselective carbonyl group reduction lead to the corresponding highly value-added anti and syn-bromohydrins with excellent diastereoselectivities. As an application, a diastereodivergent synthesis of enantiopure hemlock alkaloid (+)-α-conhydrine and its diastereomer (-)-β-conhydrine is also described.

Domaines

Chimie organique
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Dates et versions

hal-03468828 , version 1 (07-12-2021)

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Citer

Erwann Grenet, Pierre-Yves Géant, Xavier Salom-Roig. Crystallization-Induced Diastereomer Transformation of α-Bromo α′-Sulfinyl Ketones. Diastereodivergent Synthesis of (+)-α-Conhydrine and (−)-β-Conhydrine. Organic Letters, 2021, 23 (21), pp.8539-8542. ⟨10.1021/acs.orglett.1c03237⟩. ⟨hal-03468828⟩
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