Three-Component Multi-Catalytic Enantioselective Oxa-Michael/Aldolization Sequence and Application to (+)-Yashabushitriol Synthesis - MédiHAL Accéder directement au contenu
Image (Illustration) Année : 2020

Three-Component Multi-Catalytic Enantioselective Oxa-Michael/Aldolization Sequence and Application to (+)-Yashabushitriol Synthesis

Résumé

By a selective three‐component multi‐catalytic sequence, amino‐catalyzed oxa‐Michael addition of oximes to α,β‐unsaturated aldehydes has been combined with a copper‐catalyzed decarboxylative aldolization. This one‐pot procedure enables the rapid construction of functionalized ketodiol scaffolds in 85 to 94% ee. Simple reduction of both the resulting oxime and ketone functions delivered the corresponding 1,3,5‐triols of interest in a minimum of steps while considerably limiting waste generation. This methodology has been applied to the shortest (4 steps) synthesis of (+)‐yashabushitriol, highlighting the synthetic potential of this new multi‐catalytic sequence.

Dates et versions

hal-02867925 , version 1 (15-06-2020)

Licence

Domaine public

Identifiants

  • HAL Id : hal-02867925 , version 1

Citer

Céline Sperandio, Jean Rodriguez, Adrien Quintard. Three-Component Multi-Catalytic Enantioselective Oxa-Michael/Aldolization Sequence and Application to (+)-Yashabushitriol Synthesis. Illustration. France. 2020. ⟨hal-02867925⟩
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