Selective syntheses with organometallics. Part X. A convenient and diastereoselective route to homoallyl alcohols: addition of (Z)- or (E)-alkenyldimethoxyboranes to aldehydes

Fujita, Katsuramaru; Schlosser, Manfred

doi:10.1002/hlca.19820650415

research article

Selective syntheses with organometallics. Part X. A convenient and diastereoselective route to homoallyl alcohols: addition of (Z)- or (E)-alkenyldimethoxyboranes to aldehydes

Fujita, Katsuramaru

•

Schlosser, Manfred

1982

Helvetica Chimica Acta

Addn. of alkenyldimethoxyboranes to EtCHO or BzH proceeded almost completely stereospecifically; e.g., (Z)-2-butenyldimethoxyborane and EtCHO gave 62% R*,R*-EtCH(OH)CHMeCH:CH2 of 96% isomer purity; while the (E)-borane gave the R*,S* isomer in 97% purity. A transition state model was discussed. [on SciFinder (R)]