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Highly stereoselective aldol reaction of metal enolates of α-fluoropropanethioates with aldehydes affording errythro-α-fluoro-α-methyl-β-hydroxy alkanethioates1

✍ Scribed by Takashi Ishihara; Kazuyoshi Ichihara; Hiroki Yamanaka

Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
281 KB
Volume
36
Category
Article
ISSN
0040-4039

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📜 SIMILAR VOLUMES

Highly efficient and stereoselective acc
Highly efficient and stereoselective access to (Z)-α,β-difluoroallyl alcohols and (Z)-α-fluoro-α,β-unsaturated aldehydes based on the reaction of 2,3,3-trifluoro-1-propenyl p-chlorobenzenesulfonate with Grignard reagents
✍ Kazumasa Funabiki; Yoshitaka Fukushima; Tomomi Inagaki; Eiji Murata; Masaki Mats 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 254 KB

2,3,3-Trifluoro-l-pmpenyl p-chlorobenzenesulfonate (1), readily available from 2,2,3,3tetrafluoropmpanol, reacted smoothly with various Grignard reagents at 50 °(3 to afford the corresponding (Z)-a, fl-difluoroallyl alcohols 2 in moderate to excellent yields. These alcohols were smoothly hydrolyzed

The catalytic asymmetric aldol reaction
The catalytic asymmetric aldol reaction of aldehydes with unsubstituted and monosubstituted silyl ketene acetals: formation of anti-β-hydroxy-α-methyl esters
✍ Emma R. Parmee; Yaping Hong; Orin Tempkin; Satoru Masamune 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 272 KB

The title reaction with unsubstifufed and monosubstituted silyf ketene acetals proceeds with high enantioseiectivify, and in the latter case good dinstereoselecfivity favoring the anfi-/Chydrory-amethyl esters in all reported cases.