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• W2155752735 startingPage "984" @default.
• W2155752735 abstract "The synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes is reported. The β-hydroxyaminoaldehydes were prepared by enantioselective organocatalytic 1,4-addition of N-tert-butyl (tert-butyldimethylsilyl)oxycarbamate to α,β-unsaturated aldehydes (MacMillan protocol). Alkyne addition to the aldehydes followed by alcohol oxidation furnished N-Boc O-TBS-protected β-aminoynones. Removal of the TBS protecting group initiated a 7-endo-dig cyclization to yield previously unknown 3,4-dihydro-1,2-oxazepin-5(2H)-ones. Reductive cleavage of the N-O bond of the oxazepinones and Boc-deprotection provided 2-substituted 2,3-dihydropyridin-4(1H)-ones via 6-endo-trig cyclization. 2,3-Dihydropyridin-4(1H)-ones are versatile intermediates that have been used for the synthesis of many alkaloids. The new protocol allows the synthesis of 3-dihydropyridin-4(1H)-ones carrying an array of substituents at C2 that cannot be prepared from commercial β-amino acids or by one-carbon homologation of proteinogenic amino acids. The use of readily available β-hydroxylaminoaldehydes expands the utility of our previously reported method to prepare 2,3-dihydropyridin-4(1H)-ones from β-amino acids as the source of diversity and chirality. A broad substrate scope is possible because β-aminoaldehydes can be prepared from α,β-unsaturated aldehydes by an enantioselective organocatalytic process." @default.
• W2155752735 created "2016-06-24" @default.
• W2155752735 creator A5043414706 @default.
• W2155752735 creator A5046229101 @default.
• W2155752735 date "2014-01-13" @default.
• W2155752735 modified "2023-09-28" @default.
• W2155752735 title "Enantioselective Synthesis of 3,4-Dihydro-1,2-oxazepin-5(2<i>H</i>)-ones and 2,3-Dihydropyridin-4(1<i>H</i>)-ones from β-Substituted β-Hydroxyaminoaldehydes" @default.
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• W2155752735 doi "https://doi.org/10.1021/jo402445r" @default.
• W2155752735 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3985460" @default.
• W2155752735 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24785413" @default.
• W2155752735 hasPublicationYear "2014" @default.
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