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- W2765853732 abstract "We report the diastereoselective synthesis of novel spiropiperidine templates for use in SAR studies of β-secretase (BACE) inhibitors and also as versatile ligands for other receptor types. The overall synthetic approach stems from chiral starting material benzyl (S)-2-methyl-4-oxopiperidine-1-carboxylate and employs an Overman rearrangement to control the stereochemistry at the quaternary center. This process is followed by a Grubbs metathesis to close a five-membered “top” ring to form an α,β-unsaturated lactam or an α,β-unsaturated sultam. We also demonstrate that this chemistry can accommodate additional substituents on the lactam/sultam ring and allows late stage sequential functionalization of the amine and amide nitrogens to rapidly produce diverse analogues." @default.
- W2765853732 created "2017-11-10" @default.
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- W2765853732 date "2017-11-13" @default.
- W2765853732 modified "2023-09-27" @default.
- W2765853732 title "Spiropiperidine Sultam and Lactam Templates: Diastereoselective Overman Rearrangement and Metathesis followed by NH Arylation" @default.
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- W2765853732 doi "https://doi.org/10.1021/acs.joc.7b02096" @default.
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- W2765853732 hasPublicationYear "2017" @default.
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