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Discovery of Exceptionally Efficient Catalysts for Solvent-Free Enantioselective Hetero-Diels−Alder Reaction

2001; American Chemical Society; Volume: 124; Issue: 1 Linguagem: Inglês

10.1021/ja0172518

1943-2984

Long Jiang, Jieyu Hu, Xiaoqiang Shen, Bao‐Ming Ji, Kuiling Ding,

Asymmetric Hydrogenation and Catalysis

Combinatorial coordination chemistry strategy combined with high-throughput screening techniques has been successfully applied to engineering practical enantioselective catalysts for asymmetric hetero-Diels−Alder reaction. The reaction of Danishefsky's diene with a variety of aldehydes can be carried out with 0.1−0.005 mol % of H4-BINOL/Ti/H4-BINOL or H4-BINOL/Ti/H8-BINOL catalysts at room temperature under solvent- and MS-free conditions to afford dihydropyrone derivatives with up to quantitative yield and 99.8% ee.