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

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)]

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