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2004
Enantioselective syntheses
O 0031
Highly Enantioselective Copper-Catalyzed Conjugate Addition of Diethylzinc to
— New chiral monodentate phosphoramidite ligands, especially (Ia),
46- 034 Nitroalkenes.
are found to be highly effective for the enantioselective conjugate addition of diethylzinc to nitroalkenes (up to 99% e.e.). An electron-donating group at the para position
of the phenyl moiety of trans-β-nitrostyrene increases the enantioselectivity as compared to the parent trans-β-nitrostyrene, whereas an electron-withdrawing group
decreases the selectivity. An ortho substituent reduces the selectivity regardless of the
electronic nature. The catalyst (Ib) is active in the reaction of (XIII), in contrast to the
ineffectivity in the reaction of (XI). — (CHOI, H.; HUA, Z.; OJIMA*, I.; Org. Lett. 6
(2004) 16, 2689-2691; Dep. Chem., State Univ. N. Y., Stony Brook, NY 11794, USA;
Eng.) — Steudel
2004
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