Reversal of Diastereofacial Selectivity in the Addition Reaction of Organometallics to Chiral Imines
- 1 September 1991
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 20 (9) , 1555-1558
- https://doi.org/10.1246/cl.1991.1555
Abstract
It was observed that diastereofacial selectivity in the addition reaction of organometallics to the chiral imines derived from (R)-2-methoxy-1-phenylethylamine was regulated under appropriate conditions; i. e., organolithium and organocerium reagents added from the re-face of the chiral imines selectively, while organocopper reagents attacked from the si-face. The utility of the present method was demonstrated in the enantioselective synthesis of solenopsin A.Keywords
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