Copper Phosphoramidite Catalyzed Enantioselective Ring-Opening of Oxabicyclic Alkenes: Remarkable Reversal of Stereocontrol

Abstract

[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).