4.8 Article

Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol

Journal

ORGANIC LETTERS
Volume 4, Issue 16, Pages 2703-2705

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol026220u

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[GRAPHICS] An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of ant stereoselectlvity (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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