Highly diastereoselective synthesis of vinylcyclopropane derivatives with (-)-8-phenylmenthol as chiral auxiliary.
The silylated telluronium allylide 4, generated in situ from the corresponding telluronium salt in the presence of LiTMP, reacted with (-)-8-phenylmenthyl alpha,beta-unsaturated esters to afford trans-2-silylvinyl-trans-3-substituted cyclopropyl esters with high diastereoselectivity in high yields. The absolute configuration was determined by chemical transformation. A mechanistic rationale is proposed.
Ye
S
S
Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Tang
Y
Y
Dai
L X
LX
D003510:Cyclohexanes / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis*; D008610:Menthol / Q000031:analogs & derivatives / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
C435306:8-phenylmenthol; D003510:Cyclohexanes; D003521:Cyclopropanes; D014753:Vinyl Compounds; D008610:Menthol