Stereoselectivity in carbanionic additions to 2-phenylcyclohexanone

✍ Scribed by Telfer L. Thomas; Thomas A. Davidson; Ronald C. Griffith; Francis L. Scott

• Book ID: 104212874
• Publisher: Elsevier Science
• Year: 1976
• Tongue: French
• Weight: 189 KB
• Volume: 17
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71284-6

✦ Synopsis

While some stereoselectivity is frequently found in the addition of secondary enolate 1 complete stereospecificity has been rarely observed. 2 anions to dissymmetric ketones, We describe herein the reactions of a graded series of carbanions with Z-phenylcyclohexanone in which progressive increases in stereoselectivity result until finally complete stereospecificity was realized, the product being formed with a single stereochemistry about three asymmetric centers. 3 When 2-phenylcyclohexanone (I) was treated with lithium acetylide, a 1:l mixture of the cis-trans isomers of the alcohol (II) was formed.