X-ray crystal structure of a lithium aldolate - a tetrameric aggregate

✍ Scribed by Paul G. Williard; Joseph M. Salvino

• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 279 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)98690-8

✦ Synopsis

The aldol adduct formed from addition of pivalaldehyde to the lithium enolate of pinacolone crystallized directly from the reaction mixture and was subjected to x-ray diffraction analysis.

The utility of the aldol reaction in organic synthesis is undeniable. A number of recent reviews aptly summarize the current state of knowledge concerning this and related reactions.' In most cases, comparative product analysis provides the basis for thinking about the reactions' mechanistic and stereochemical aspects. However, some kinetic analyses as well as a molecular mechanical interpretation2 of the aldol reaction are reported. Recent x-ray diffraction analyses of lithium anions' from this and other labs led us to consider a crystallographic study of the aldol reaction.

Hence, we now report the first single crystal, x-ray structure determination of a lithiated aldol intermediate.