title: Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde.
abstract: For the first time, the L-proline-catalyzed direct asymmetric self-aldolization of acetaldehyde is described affording (+)-(5S)-hydroxy-(2E)-hexenal 2 with ee's ranging from 57 to 90%. Further transformations of 2 into synthetically valuable building blocks are presented. A mechanism for the formation of 2 is proposed.
authors.affiliation: The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Armando
authors.initials: A
authors.lastname: Córdova
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Notz
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000079:Acetaldehyde / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis*; D002384:Catalysis; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C450851:5-hydroxyhexenal; D000447:Aldehydes; D011392:Proline; D000079:Acetaldehyde