The stereochemistry of high pressure aldehyde addition to allylstannanes

✍ Scribed by Neil S. Isaacs; Raymond L. Marshall; David J. Young

• Book ID: 104216070
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 131 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79589-x

✦ Synopsis

The high pressure (9 kbar, 3oOC) mediated addition of benzaldehyde to allylstannane (1) occurs stereospecifically with syn approach of the electrophile. At 6OoC, the reaction is less selective, probably due to some isomerization of cis (1) to trun.s (1). At both temperatures good erythro diastexeoselectivity is observed.

The addition of aldehydes to allylstannanes requires either heat, high-pressure or the addition of a Lewis acid'.