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3342889220
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note
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In acetonitrile, which is the solvent of choice for Cu(II)-catalyzed conjugate additions of carbamates (see ref 13b), the asymmetric reaction did not proceed. THF was also found to be ineffective (<5% conversion after 2 days). Diethyl ether generally showed results comparable to those attained in methylene chloride, although in certain instances the enantioselectivity was essentially perfect (for example, product 11a 92% yield, ≥99% ee; 11b, 95% yield, ≥99% ee).
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For problems inherent to the conjugate addition of N-nucleophiles to β-aryl enoyl systems, and a solution to them, see: ref 11c. Also see: ref 11e-g.
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See Supporting Information for details.
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At the present stage, proposals for consistent catalytic cycle and transitionstate models seem premature. One reviewer has suggested an eight-membered transition state involving copper coordination.
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