期刊
NATURE
卷 483, 期 7389, 页码 315-319出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/nature10932
关键词
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资金
- Max Planck Sociey
- European Research Council
Acetals are molecular substructures that contain two oxygencarbon single bonds at the same carbon atom, and are used in cells to construct carbohydrates and numerous other molecules. A distinctive subgroup are spiroacetals, acetals joining two rings, which occur in a broad range of biologically active compounds, including small insect pheromones and more complex macrocycles(1,2). Despite numerous methods for the catalytic asymmetric formation of other commonly occurring stereocentres, there are few approaches that exclusively target the chiral acetal centre and none for spiroacetals(3,4). Here we report the design and synthesis of confined Bronsted acids based on a C-2-symmetric imidodiphosphoric acid motif, enabling a catalytic enantioselective spiroacetalization reaction. These rationally constructed Bronsted acids possess an extremely sterically demanding chiral microenvironment, with a single catalytically relevant and geometrically constrained bifunctional active site. Our catalyst design is expected to be of broad utility in catalytic asymmetric reactions involving small and structurally or functionally unbiased substrates.
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