Oxabicic1o vinil sulfonas: Rotura alquilante directa del puente con reactivos organolíticos
Abstract
Se describe una interesante rotura alquilante regio-y estereocontrolada del puente de
oxabiciclo vinil sulfonas. Las 7-oxabiciclo[2.2.1] heptenil y 8-oxabiciclo [3.2.1.] octenil
sulfonas sufren aperturas syn S~' cuando se tratan con una amplia variedad de reactivos
organolíticos e hiduro de litio y aluminio. De esta forma, se obtienen ciclohexenil y
cicloheptenil sulfonas, altamente funcionalizadas, que son intermedios sintéticos versátiles.
La completa estereoselectividad encontrada en la adición conjugada exo puede explicarse
en base a la quelación del reactivo organometálico con el oxígeno puente.
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References
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