The reaction of lithium trialkylalkynylborates with oxiranes producing γ-hydroxyketones and trisubstituted olefins of definite configuration

✍ Scribed by Mikio Naruse; Kiitiro Utimoto; Hitosi Nozaki

• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 218 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)96127-1

✦ Synopsis

In continuation of the studies on synthetic applications of trialkyl-l-alkynylborates (I), " 2 the present paper discloses a novel reaction of I with oxiranes II affording non-isolable intermediates III, from which we have obtained r-hydroxyketones V, trisubstituted olefins VI, and a tetrasubstituted olefin VII upon the appropriate work-up in three different ways. To a solution of 1-heptyne (0.48 g, 5.0 mmol) in THF (5. 0 ml) at 0' under nitrogen atmosphere, butyllithium (5. 0 mmol in 5.0 ml of hexane) was added and stirring was continued