Ylide modeling as the key to a cis-selective synthesis of stilbenes

Stilbene type olefins can be prepd. with cis-stereoselectivities approaching 95:5 if tris(2-methoxymethoxyphenyl)phosphine derived ylides are employed and the reaction is carried out at -75 Deg. Thus, treating phosphonium ylide I with p-MeOC6H4CHO in THF contg. LiBr 2.5 h at -75 Deg gave 99% stilbenes II with a Z/E ratio of 96:4. [on SciFinder (R)]


Published in:
Synlett, 10, 605-8
Year:
1990
Keywords:
Note:
CAN 114:101210
25-2
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chem. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0936-5214
written in English.
128399-09-7 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with aldehydes, stilbenes and alkenes from); 128399-10-0; 132313-22-5; 132313-23-6; 132313-24-7; 132313-25-8; 132313-26-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of ylide from, and its reaction with aldehydes); 1149-56-0P; 1657-53-0P; 1694-19-5P; 1898-14-2P; 2510-75-0P; 10201-58-8P; 10201-59-9P; 13041-79-7P; 14064-41-6P; 14064-68-7P; 14168-83-3P; 15638-14-9P; 22257-16-5P; 42134-70-3P; 42134-74-7P; 52805-92-2P; 53423-25-9P; 124562-04-5P; 132312-98-2P; 132312-99-3P; 132313-13-4P; 132313-14-5P; 132313-15-6P; 132313-16-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by reaction of tris(methoxymethoxyphenyl)phosphonium ylides with aldehyde); 132313-17-8; 132313-18-9; 132313-19-0; 132313-20-3; 132313-21-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with benzaldehyde); 66-25-1 (Hexanal); 505-57-7 (2-Hexenal); 2579-21-7 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with tris(methoxymethoxyphenyl)phosphonio(phenylmethanide), stereoisomeric alkene from); 100-52-7 (Benzaldehyde); 105-07-7 (p-Cyanobenzaldehyde); 123-11-5 (p-Methoxybenzaldehyde); 455-19-6 (p-(Trifluoromethyl)benzaldehyde); 529-20-4 (o-Methylbenzaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with tris(methoxymethoxyphenyl)phosphonio(phenylmethanide), stereoisomeric stilbenes from)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)