SCOOPY-Reaktionen : Stereoselektivität der Allylalkohol-Synthese via Betain-Ylide
Schlosser, Manfred; Coffinet, D.
1971

Abstract

The stereoselectivity of the SCOOPY reaction, in which allyl alc. derivs. are prepd. by reaction of betaine ylides with carbonyl compds., was investigated by the synthesis of 1-hydroxy-2-octene (I), and 1-hydroxymethyl-2-octene (II) from Ph3P+-CH2 and Ph3P+-CHMe, resp., using HCHO and octanal. Treatment of III with HCHO in the presence of LiBr followed by treatment with n-C5H11CHO gave 10% I having a 97:3 cis-trans ratio. A 36% yield of II with a 30:70 cis-trans ratio was obtained by treating III with n-C5H11CHO and then with HCHO. Treatment of Ph3P+-CHMe with n-C5H11CHO and then with HCHO gave 71% II with a 99.3:0.7 cis-trans ratio, while treatment with HCHO and then with n-C5H11CHO gave 48% II with a 36:64 ratio. [on SciFinder (R)]

Details

Title SCOOPY-Reaktionen : Stereoselektivität der Allylalkohol-Synthese via Betain-Ylide
Author(s) Schlosser, Manfred ; Coffinet, D.
Published in Synthesis
Issue 7
Pages 380-1
Date 1971
ISSN 0039-7881
Keywords
Note CAN 75:117901
22
Physical Organic Chemistry
Org. Chem. Inst.,Univ. Heidelberg,Heidelberg,Fed. Rep. Ger.
Journal
written in German.
33965-54-7P; 33965-55-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 1754-88-7; 3487-44-3; 19493-09-5; 19493-10-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with caproaldehyde and formaldehyde); 66-25-1 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with formaldehyde and phosphorus ylides); 50-00-0 Role: RCT (Reactant), RACT (Reactant or reagent) (with phosphorus ylides and caproaldehyde)
DOI https://doi.org/10.1055/s-1971-21748
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
Record creation date 2006-03-03