Synlett 1994; 1994(5): 351-352
DOI: 10.1055/s-1994-22851
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Enantiocontrolled Conjugate Addition of Chiral Alkoxydimethylcuprate to Macrocyclic Enones

K. Tanaka* , J. Matsui, K. Somemiya, H. Suzuki
  • *Department of Chemistry, Faculty of Science, Kyoto University, Kitashirakawa, Sakyo, Kyoto 606, Japan
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Publication History

Publication Date:
22 March 2002 (online)

The asymmetric conjugate addition reactions of the chiral organocuprate, prepared from (1R, 2R, 3S, 4S)-3-[(1-methyl-pyrrol-2-yl) methylamino]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (1) with ten-to eighteen-membered ring enones afforded chiral cyclic ketones in 52-99% enantiomeric excess (ee). The conjugate addition to (Z)-cycloalkenones (C10 and C11) gave the S-configuration of chiral 3-methylketones, whereas the reaction with (E)-cycloalkenones (C11, C12, C13, C14, C15, C16, and C17) gave (R)-ketones.

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