Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol.
[reaction: see text] An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of anti-stereoselectivity (up to anti/syn >99:1), complementary to the Pd(0)-catalyzed syn-selective ring-opening protocol, allowing a new entry to anti-dihydronaphthols with high enantioselectivity (up to 99% ee).
Bertozzi
Fabio
F
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, The Netherlands.
Pineschi
Mauro
M
Macchia
Franco
F
Arnold
Leggy A
LA
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL