Catalytic Asymmetric Synthesis of 2,2-Disubstituted Terminal Epoxides via Dimethyloxosulfonium Methylide Addition to Ketones

Catalytic Asymmetric Synthesis of 2,2-Disubstituted Terminal Epoxides via Dimethyloxosulfonium Methylide Addition to Ketones

Catalytic asymmetric Corey−Chaykovsky epoxidation of ketones with dimethyloxosulfonium methylide 2 using an LLB 1a + Ar3PO complex proceeded smoothly at room temperature, and 2,2-disubstituted terminal epoxides were obtained in high enantioselectivity (91−97%) and yield (>88−99%) from a broad ra...

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Veröffentlicht in:Journal of the American Chemical Society 2008-08, Vol.130 (31), p.10078-10079
Hauptverfasser: Sone, Toshihiko, Yamaguchi, Akitake, Matsunaga, Shigeki, Shibasaki, Masakatsu
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Epoxy Compounds - chemical synthesis
Ketones - chemistry
Organophosphorus Compounds
Sulfonium Compounds - chemistry
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Zusammenfassung:Catalytic asymmetric Corey−Chaykovsky epoxidation of ketones with dimethyloxosulfonium methylide 2 using an LLB 1a + Ar3PO complex proceeded smoothly at room temperature, and 2,2-disubstituted terminal epoxides were obtained in high enantioselectivity (91−97%) and yield (>88−99%) from a broad range of methyl ketones with 1−5 mol % catalyst loading. The use of achiral additive Ar3PO 5i was important to achieve high enantioselectivity.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja803864p