title: HMPA promotes retro-aldol reaction, resulting in syn-selective addition of lithiated 1-naphthylacetonitrile to aromatic aldehydes
abstract: In HMPA-THF solution, lithiated 1-naphthylacetonitrile undergoes highly syn-selective addition to aromatic aldehydes, providing the first access to such syn-aldols. Syn-selectivity is also observed with two other arylacetonitriles. Aldolate equilibration and crossover experiments demonstrate that HMPA promotes retro-aldol reaction and that aldol diastereoselectivity under these conditions is thermodynamically controlled.
authors.affiliation: Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong.
authors.initials: PR
authors.lastname: Carlier
authors.initials: CW
authors.lastname: Lo
authors.initials: MM
authors.lastname: Lo
authors.initials: NC
authors.lastname: Wan
authors.initials: ID
authors.lastname: Williams