Copper Phosphoramidite Catalyzed Enantioselective Ring-opening Of Oxabicyclic Alkenes: Remarkable Reversal Of Stereocontrol
- Feringa, B.L.,
- Bertozzi, F.,
- Pineschi, M.,
- Macchia, F.,
- Arnold, L.A.,
- Minnaard, A.J.,
DOIAbstract
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).
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