Copper Phosphoramidite Catalyzed Enantioselective Ring-Opening of Oxabicyclic Alkenes: Remarkable Reversal of Stereocontrol
- 4 July 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (16) , 2703-2705
- https://doi.org/10.1021/ol026220u
Abstract
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).Keywords
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