We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
A Direct, Concise, and Enantioselective Synthesis of 2-Substituted 4,4,4-Trifluorobutane-1,3-diols Based on the Organocatalytic In Situ Generation of Unstable Trifluoroacetaldehyde.
- Authors
Funabiki, Kazumasa; Furuno, Yudai; Yano, Yosuke; Sakaida, Yuta; Kubota, Yasuhiro; Matsui, Masaki
- Abstract
A direct, concise, and enantioselective synthesis of 2-substituted 4,4,4-trifluorobutane-1,3-diols based on the organocatalytic asymmetric direct aldol reaction of an ethyl hemiacetal of trifluoroacetaldehyde with various aldehydes was examined. A catalytic amount (30 mol%) of commercially available and inexpensive l-prolinamide is quite effective as an organocatalyst for the catalytic in situ generation of gaseous and unstable trifluoroacetaldehyde from its hemiacetal, and a successive asymmetric direct aldol reaction with various aldehydes in dichloromethane at 0°C, followed by reduction with sodium borohydride, gives 2-substituted 4,4,4-trifluorobutane-1,3-diols in moderate to good yields (31-84%) with low diastereoselectivities and good to excellent enantioselectivities (64-97% ee).
- Subjects
ENANTIOSELECTIVE catalysis; BUTANE; GLYCOL synthesis; ORGANOCATALYSIS; ACETALDEHYDE
- Publication
Chemistry - An Asian Journal, 2015, Vol 10, Issue 12, p2701
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201500607