The reductive cleavage of the benzenseleno-group in trans-β-hydroxyselenides, to yield a stereogenic methyne center, has been investigated. When the reaction is carried out with lithium in diethylamine, the equilibrated carbanionic intermediate traps the proton of the neighbouring hydroxy function, blocking the stereogenic center as a product with a predictable chirality. Using this strategy, several natural monoterpenes in enantiomerically pure form have been prepared.
Influence of a hydroxy group in the asymmetric reduction of selenides: enantioselective synthesis of naturally occurring monoterpenes
Ceccherelli, Paolo;Curini, Massimo;Marcotullio, Maria Carla;Rosati, Ornelio
1998
Abstract
The reductive cleavage of the benzenseleno-group in trans-β-hydroxyselenides, to yield a stereogenic methyne center, has been investigated. When the reaction is carried out with lithium in diethylamine, the equilibrated carbanionic intermediate traps the proton of the neighbouring hydroxy function, blocking the stereogenic center as a product with a predictable chirality. Using this strategy, several natural monoterpenes in enantiomerically pure form have been prepared.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
