The alkylation of thexyldialkylalkynylborates - a new stereoselective trisubstituted olefin synthesis.

✍ Scribed by Andrew Pelter; C. Subrahmanyam; R.J. Laub; Ken J. Gould; C.R. Harrison

• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 212 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)72218-0

✦ Synopsis

The major product from the alkylation of thexyldialkylalkynylborates is the vinylborane in which the groups derived from the alkylating agent and from migration from boron to carbon are cis to each other. -We have recently defined conditions for the alkylation of trialkylalkynylborates (VI) leading to intermediates which on oxidation give ketones (VII) in excellent yields (see Scheme).' The alkylation/migration process however is not stereospecific. and hydrolysie gives mixtures of the olefins (IV) and (V). " " 3