- STADIES ON THE WITTIG REACTION (VIII). STEREOSELECTIVITY OF DIPHENYL ALLYLIC PHOSPHONIUM YLIDS IN WITTIG REACTION
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Ylids generated from diphenyl allylic phosphonium salts reacted with aliphatic aldehydes containing a terminal oxygen functionized group in the absence of lithium salt to give E,E-conjugated dienes.The stereoselectivity depends mainly on the base used, the allylic part of phosphonium salts also shows some effect on stereochemistry.Eight conjugated dienic insect sex pheromones and related analogues with different E-selectivities were obtained.
- Wenfang, Huang,Jun, Zhu,Wenjing, Xiao,Yanneng, Deng
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- Ethylaluminum Dichloride Catalyzed Ene Reactions of Aldehydes with Nonnucleophilic Alkenes
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Ethylaluminum dichloride, which is a strong Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic aldehydes with nonnucleophilic alkenes.Higher aldehydes give good yields of ene adducts with terminal alkenes.Formaldehyde gives good yields of adducts with electron-deficient alkenes.This reaction has been used for the synthesis of recifeiolide, ricinelaidic acid, and the insect pheromones (E,E)-8,10-dodecadienyl acetate and (E)-9,11-dodecadienyl acetate.
- Snider, Barry B,Phillips, Gary B.
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p. 464 - 469
(2007/10/02)
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