Asymmetric hydrosilylation of olefins catalyzed by a chiral ferrocenylphosphine-palladium complex. Asymmetric synthesis of optically active alcohols and bromides from olefins

✍ Scribed by Tamio Hayashi; Kohei Tamao; Yoshio Katsuro; Ichiro Nakae; Makoto Kumada

• Publisher: Elsevier Science
• Year: 1980
• Tongue: French
• Weight: 223 KB
• Volume: 21
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)92802-8

✦ Synopsis

swmnary : Optically active norbornyl and l-phenylethyl alcohols and bromides were obtained, res- pectively, from norbornyl-and l-phenylethylpentafluorosilicates which were prepared by asymmetric hydrosilylation of norbornene and styrene with trichlorosilane catalyzed by a chiral ferrocenylphosphine-palladium complex followed by treatment with potassium fluoride.

The most efficient and promising use of chiral reagents for asymmetric syntheses is their use as catalysts. Although several kinds of asymmetric syntheses' have been developed for preparing optically active alcohols or halides from prochiral olefins by use of stoichiometric amounts of chiral reagents, e.g., di-3-pinanylborane,2 no catalytic procedure has been known for such reactions. Here we report a new approach to catalytic asymmetric synthesis of certain Chem., 118, 331 (1976); (c) Y.