Catalytic cyclization is one of the most efficient methods to synthesize 2-monosubstituted indoles and benzofurans from o-alkynylanilines and -phenols. Recently, transition metal catalyzed cyclization of o-alkynylanilines, -phenyl ethers, and -phenyl sulfides bearing a migration group (E) on the heteroatom (Y) has attracted much attention as a direct method to synthesize the 2,3-disubstituted indoles, benzofurans, and benzo[b]thiophenes, which have been widely utilized as medicines and organic materials (Scheme 1). However, the nature of this [1,3] migration has rarely been elucidated to date. Here we report that chirality transfer in the gold-catalyzed carbothiolation of o-alkynylphenyl 1-aryl ethyl sulfides proceeds with retention of stereocenter at the migration group.
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