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

Sperandio Céline | Zendy; Rodriguez Jean | Zendy; Quintard Adrien | Zendy

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

Author(s) -

Sperandio Céline,

Rodriguez Jean,

Quintard Adrien

Publication year - 2020

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202000185

Subject(s) - michael reaction , oxime , enantioselective synthesis , sequence (biology) , ketone , catalysis , limiting , component (thermodynamics) , chemistry , combinatorial chemistry , organic chemistry , stereochemistry , engineering , biochemistry , physics , mechanical engineering , thermodynamics

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.

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