2-Alkenyldiphenylphosphine oxides and PO-ylides derived thereof in trans selective Horner-Wittig olefination reactions

Allylic PO-ylides generated by deprotonation of 2-alkenyldiphenylphosphine oxides with BuLi were used to prep. 1,3-dienes trans-selectively. The (Z/E) ratios of the newly formed double bond are 1:99 when straight-chain, while they were 2:98 to 4:96 when b-branched aliph., and 4:96 to 6:94 when arom. aldehydes were employed. [on SciFinder (R)]


Published in:
Synlett, 12, 1195-1196
Year:
1996
Keywords:
Note:
CAN 126:103682
21-2
General Organic Chemistry
Institut Chemie Organique,Universite Lausanne,Lausanne,Switz.
Journal
0936-5214
written in English.
100-52-7 (Benzaldehyde); 124-19-6 (Nonanal); 2043-61-0 (Cyclohexanaldehyde); 4141-48-4 (Allyldiphenylphosphine oxide); 4455-75-8; 13303-60-1; 13303-61-2 Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective Horner-Wittig olefination with alkenyldiphenylphosphine oxides); 17668-60-9P; 58322-08-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (stereoselective Horner-Wittig olefination with alkenyldiphenylphosphine oxides); 3909-96-4P; 16939-57-4P; 25203-83-2P; 39491-73-1P; 87921-45-7P; 88001-21-2P; 114444-89-2P; 156049-84-2P; 185962-93-0P; 185962-94-1P; 185962-95-2P; 185962-96-3P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective Horner-Wittig olefination with alkenyldiphenylphosphine oxides)
Laboratories:




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


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