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A preliminary survey of strategies for the asymmetric cycloaddition of nonstabilized 2-azaallyllithiums with alkenes is reported. The chiral diamine (-)-sparteine exerted little, if any, absolute stereocontrol. The attachment of a chiral auxiliary to the anion was more successful, leading to the first example of an asymmetric cycloaddition of a 2-azaallyllithium (24 to 25, 98% e.e.).
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