Abstract
(E)-RCH:CH(CH2)nOH (n = 2,3,5,7; R = Et, pentyl, hexyl, E-CH:CHMe) were obtained in 69-78% yield in a 1-pot reaction by treating HO(CH2)nCH2P+Ph3 Br- with PhLi in tetrahydrofuran-EtiO, followed by addn. of RCHO, treatment with HCl-Et2O, and with KOCMe3. [on SciFinder (R)]
Details
Title
The betaine-ylide route to trans-alkenols
Author(s)
Schlosser, Manfred ; Huynh Ba, Tuong ; Schaub, Bruno
Published in
Tetrahedron Letters
Volume
26
Issue
3
Pages
311-14
Date
1985
ISSN
0040-4039
Keywords
Wittig reaction (of betaine ylides); Ylides Role: SPN (Synthetic preparation); PREP (Preparation) (phosphorus betaine; prepn. and Wittig reaction of); Pheromones Role: SPN (Synthetic preparation); PREP (Preparation) (trans-alkenols; prepn. of; by Wittig; Wittig hydroxyalkylidenephosphorane; alkenol trans
Note
CAN 103:6068
26-2
Biomolecules and Their Synthetic Analogs
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
66-25-1; 111-71-7; 123-38-6; 123-73-9 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with hydroxyalkylidene phosphoranes); 10339-60-3P; 10339-62-5P; 31502-19-9P; 42513-42-8P; 89995-99-3P; 96854-18-1P; 96854-19-2P; 96854-20-5P Role: RCT (Reactant), PREP (Preparation), RACT (Reactant or reagent) (formation and Wittig reaction of, with aldehydes); 96854-21-6P; 96854-22-7P; 96854-23-8P; 96881-36-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 51860-45-8; 65734-62-5; 68760-65-6; 87436-78-0 Role: PROC (Process) (ylide formation of, with phenyllithium)
26-2
Biomolecules and Their Synthetic Analogs
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
66-25-1; 111-71-7; 123-38-6; 123-73-9 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with hydroxyalkylidene phosphoranes); 10339-60-3P; 10339-62-5P; 31502-19-9P; 42513-42-8P; 89995-99-3P; 96854-18-1P; 96854-19-2P; 96854-20-5P Role: RCT (Reactant), PREP (Preparation), RACT (Reactant or reagent) (formation and Wittig reaction of, with aldehydes); 96854-21-6P; 96854-22-7P; 96854-23-8P; 96881-36-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 51860-45-8; 65734-62-5; 68760-65-6; 87436-78-0 Role: PROC (Process) (ylide formation of, with phenyllithium)
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