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Asymmetric α-Alkylation of <i>N</i><i>‘</i>-<i>tert</i>-Butanesulfinyl Amidines. Application to the Total Synthesis of (6<i>R</i>,7<i>S</i>)-7-Amino-7,8-dihydro-α-bisabolene

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A highly diastereoselective α-alkylation of N‘-tert-butanesulfinyl amidines has been developed along with methods for converting the alkylation products to enantiomerically enriched amines that incorporate both α- and β-stereocenters. The utility of this chemistry is further demonstrated by the first asymmetric synthesis of the antimicrobial marine natural product (6R,7S)-7-amino-7,8-dihydro-α-bisabolene.

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2016-05-06
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