Three‐Component Multi‐Catalytic Enantioselective Oxa‐Michael/Aldolization Sequence and Application to (+)‐Yashabushitriol Synthesis. Issue 17 (5th March 2020)

• Record Type: Journal Article
• Authors: Sperandio, Céline; Rodriguez, Jean; Quintard, Adrien
• Is Part Of: European journal of organic chemistry. Issue 17(2020)
• Page Start: 2493
• Page End: 2496
• Publication Date: 2020-03-05
• Subjects: Aldolization -- Copper -- Multicatalysis -- Organocatalysis -- Polyketides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000185
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : By a selective multi‐catalytic sequence, organocatalyzed oxa‐Michael addition of oximes to α‐, β‐unsaturated aldehydes has been combined with a decarboxylative aldolization. This multi‐component procedure enables a rapid construction of extended 1, 3‐polyols scaffolds in 85 to 94% ee highlighted in the 4 steps synthesis of (+)‐yashabushitriol.