Abstract
Di-, tri- and tetra-substituted oxetane derivatives with combinations of ester, amide, nitrile, aryl, sulfone and phosphonate substituents are prepared as fragments or building blocks for drug discovery. The synthesis of these novel oxetane functional groups, in new chemical space, is achieved via rhodium-catalysed O-H insertion and C-C bond forming cyclisation.
Highlights
Di, tri- and tetra-substituted oxetane derivatives with combinations of ester, amide, nitrile, aryl, sulfone and phosphonate substituents are prepared as fragments or building blocks for drug discovery
We recently reported the preparation of 2-sulfonyl oxetanes, formed through a novel anionic C–C bond forming cyclisation (Scheme 1A).[16]
These fragments displayed good pH stability, and stability to liver microsomes.16b We have established an efficient synthesis of oxetane 2,2dicarboxylates involving O–H insertion using diazomalonates, and C–C bond forming cyclisation (Scheme 1B).[17]
Summary
Di-, tri- and tetra-substituted oxetane derivatives with combinations of ester, amide, nitrile, aryl, sulfone and phosphonate substituents are prepared as fragments or building blocks for drug discovery. The synthesis of these novel oxetane functional groups, in new chemical space, is achieved via rhodium-catalysed O–H insertion and C–C bond forming cyclisation. Scheme 1 Synthesis of oxetanes through anionic C–C bond forming cyclisation.
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