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)]
1982
65
4
1258
1263
CAN 97:197798
23-7
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
123-38-6 Role: RCT (Reactant), RACT (Reactant or reagent) (addn. reaction of, with alkenyldimethoxyboranes); 76347-09-6; 76347-11-0 Role: RCT (Reactant), RACT (Reactant or reagent) (addn. reaction of, with benzaldehyde or propanal); 100-52-7 Role: RCT (Reactant), RACT (Reactant or reagent) (addn. reaction of, with butenyldimethoxyborane); 83552-85-6; 83552-86-7; 83552-87-8; 83552-88-9 Role: RCT (Reactant), RACT (Reactant or reagent) (addn. reaction of, with propanal); 1502-85-8P; 1538-21-2P; 1589-07-7P; 52922-10-8P; 52922-19-7P; 83552-89-0P; 83552-90-3P; 83552-91-4P; 83552-92-5P; 83552-93-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
REVIEWED
EPFL