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

Fujita, KatsuramaruSchlosser, Manfred2006-03-032006-03-032006-03-03198210.1002/hlca.19820650415https://infoscience.epfl.ch/handle/20.500.14299/226805Addn. 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)]Regiochemistry (in addn. reaction of alkenylboranes with benzaldehyde or propanal); Stereochemistry (of addn. reaction of alkenylboranes with benzaldehyde or propanal); Addition reaction (of alkenylboranes with benzaldehyde or propanalstereochem. of)alkenylborane addn aldehyde stereochem; borane alkenyl addn aldehyde; propanal addn alkenylborane stereochem; benzaldehyde addn alkenylborane stereochemSelective syntheses with organometallics. Part X. A convenient and diastereoselective route to homoallyl alcohols: addition of (Z)- or (E)-alkenyldimethoxyboranes to aldehydestext::journal::journal article::research article