Lewis acid-promoted rearrangement of 2,3-epoxy alcohol derivatives: stereochemical control and selective formation of two types of chiral quaternary carbon centers from the single carbon skeleton.
The Lewis acid-promoted rearrangement of 2,2,3,3-tetrasubstituted 2,3-epoxy alcohols with several kinds of protecting groups was investigated. When SnCl4 is used as a Lewis acid, the reaction proceeds in a regio- and stereo-controlled manner to afford two types of carbonyl compounds selectively from a single 2,3-epoxy alcohol only by changing the protecting group of the alcohol. The method was then applied to the formation of two types of acyclic and cyclic quaternary carbon centers from the single compound in optically active forms.
Kita
Yasuyuki
Y
Graduate School of Pharmaceutical Sciences, Osaka University, Yamadaoka 1-6, Suita, Osaka 565-0871, Japan. kita@phs.osaka-u.ac,jp
Matsuda
Satoshi
S
Inoguchi
Ryoko
R
Ganesh
Jnaneshwara K
JK
Fujioka
Hiromichi
H
D000438:Alcohols / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry*
D000438:Alcohols; D004852:Epoxy Compounds; D007659:Ketones; D017971:Tin Compounds; C041694:stannic chloride; D002244:Carbon