Selective syntheses with organometallics. Part X. A convenient and diastereoselective route to homoallyl alcohols: addition of (Z)- or (E)-alkenyldimethoxyboranes to aldehydes
1982
Abstract
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)]
Details
Title
Selective syntheses with organometallics. Part X. A convenient and diastereoselective route to homoallyl alcohols: addition of (Z)- or (E)-alkenyldimethoxyboranes to aldehydes
Author(s)
Fujita, Katsuramaru ; Schlosser, Manfred
Published in
Helvetica Chimica Acta
Volume
65
Issue
4
Pages
1258-1263
Date
1982
ISSN
0018-019X
Keywords
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 propanal; stereochem. of); alkenylborane addn aldehyde stereochem; borane alkenyl addn aldehyde; propanal addn alkenylborane stereochem; benzaldehyde addn alkenylborane stereochem
Note
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)
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)
Laboratories
LSCO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2006-03-03