title: Catalytic asymmetric synthesis of stable oxetenes via Lewis acid-promoted [2+2] cycloaddition.
abstract: A highly enantioselective and atom-economical [2 + 2] cycloaddition of various alkynes with trifluoropyruvate using a dicationic (S)-BINAP-Pd catalyst has been established. This is the first enantioselective synthesis of stable oxetene derivatives, whose structure has been clarified by X-ray analysis. This catalytic process offers a practical synthetic method for oxetene derivatives (catalyst loading: up to 0.1 mol %), which can serve as novel chiral building blocks for pharmaceuticals and agrochemicals and can also be transformed into a variety of enantiomerically enriched CF(3)-substituted compounds with high stereoselectivity.
authors: Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan.
authors: Kohsuke
authors: K
authors: Aikawa
authors: Yūta
authors: Y
authors: Hioki
authors: Natsumi
authors: N
authors: Shimizu
authors: Koichi
authors: K
authors: Mikami
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D058116:Lewis Acids / Q000737:chemistry*; D008958:Models, Molecular
chemical_list: D000480:Alkynes; D058116:Lewis Acids