1-Lithio-1-benzenesulfinyl-2-trimethylsilylethane as a 2-trimethylsilylvinyl anion equivalent in reactions with aldehydes, ketones and epoxides

✍ Scribed by C-N. Hsiao; H. Shechter

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 256 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81928-0

✦ Synopsis

Aldehydes, ketones and epoxides give adducts with l-lithio-1-benzenesulfinyl-2-trimethylsilylethane which upon neutralization eliminate benzenesulfenic acid efficiently at 76'C to yield trans-3-(trimethylsilyl)allyl alcohols and trans-4-(trimethylsilyl)-3-alken-1-01s. 3-(Trimethylsilyl)allyl alcohols (1) and B-trimethylsilylvinyl aldehydes (2, R=H) and ketones (2, R=alkyl and aryl) are important in synthesis. la-g In this laboratory derivatives of 1 and 2 are of interest with respect to their cationic (3) and carbenic (4) intermediates. Preparations of 1 have previously involved (1) condensations of carbonyl compounds with trans-2-trimethylsilylvinylmetallo reagents (5, Eq. l), lc,e,g c2j reactions of aldehydes and ketones with metallotrimethylsilylacetylenes (6, Eq. 1) followed by partial reduction (H2/Pd/C or LiAlH4) of the triple bonds la,b,d,f and (3) addition of organometallics to 2. If Although the