Diastereoselective synthesis of useful building blocks by crotylation of beta-branched alpha-methylaldehydes with potassium crotyltrifluoroborates.
The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of beta-branched alpha-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium ( E)-crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.
Tanaka
Kyosuke
K
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Fujimori
Yukiko
Y
Saikawa
Yoko
Y
Nakata
Masaya
M
D000447:Aldehydes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D001881:Borates; D002073:Butanes; C005556:propionaldehyde