Enantiocontrolled Conjugate Addition of Chiral Alkoxydimethylcuprate to Macrocyclic Enones
- 1 January 1994
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1994 (05) , 351-352
- https://doi.org/10.1055/s-1994-22851
Abstract
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.Keywords
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