Die Horner-Variante der Wittig-Reaktion : unter milden Bedingungen durchführbar und mit stereochemischen Optionen ausgestattet

Metalated phenylphosphine oxides reacted with aldehydes at room temp. to give trans olefins with high selectivity. Thus, Ph2P(O)CH2Ph was treated with BuLi, then with PhCHO to give 78% trans-stilbene. The configuration of a double bond present in the starting material was conserved throughout the reaction sequence, e.g., (E)-Ph2P(O)CH:CHMe reacted with BuLi and PrCHO to give 28% (E,E)-MeCH:CHCH:CHPr, with only traces of the other isomers. [on SciFinder (R)]


Published in:
Chimia, 30, 3, 197-9
Year:
1976
Keywords:
Note:
CAN 85:176734
23-2
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0009-4293
written in German.
2959-74-2; 17668-60-9 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with aldehydes); 1733-57-9 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with benzaldehyde, stereoselective); 103-30-0P; 873-66-5P; 60919-80-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by Wittig reaction, stereoselective); 123-72-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with diphenylbutenylphosphine oxide); 100-52-7 Role: RCT (Reactant), RACT (Reactant or reagent) (with diphenylbenzylphosphine oxide)
Laboratories:




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


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