Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde.
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.
Córdova
Armando
A
The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Notz
Wolfgang
W
Barbas
Carlos F
CF
D000079:Acetaldehyde / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis*; D002384:Catalysis; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
C450851:5-hydroxyhexenal; D000447:Aldehydes; D011392:Proline; D000079:Acetaldehyde