Regio- and diastereoselective reductive coupling of vinylepoxides catalyzed by titanocene chloride.
[reaction: see text] The Ti(III)-catalyzed reaction of a series of vinylepoxides leads, with regio- and E-diastereoselectivity control, to good-to-excellent yields of the corresponding homocoupling products. This homocoupling reaction, which involves a new C-C bond-forming method, takes place via a S(N)2' process between an allyltitanium species and the starting vinylepoxide. The process can be used for the rapid and efficient formation of highly valuable intermediates for organic synthesis, as well as new interesting homologues of natural products.
Barrero
Alejandro F
AF
Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda. Fuentenueva, 18071 Granada, Spain. afbarre@goliat.ugr.es
Quílez del Moral
José F
JF
Sánchez
Elena M
EM
Arteaga
Jesús F
JF