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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.