- A convenient synthetic route to enantiopure N-tosylazetidines from α-amino acids
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A general and convenient synthetic route to various chiral 2-substituted- and 2,4-disubstituted-N-tosylazetidines (ee >99%) is described in good overall yields starting from chiral α-amino acids using very simple chemistry.
- Ghorai, Manas K.,Das, Kalpataru,Kumar, Amit
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p. 2471 - 2475
(2007/10/03)
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- Wolff rearrangement of diazo ketones derived from N-p-tolylsulfonyl-protected α- and β-amino acids
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Diazo ketones derived from N-p-tolylsulfonyl (tosyl)-protected α- and β-amino acids have been synthesized and their diazo decomposition under standard Wolff rearrangement conditions, PhCO2Ag-Et3N-MeOH, has been investigated. It is observed that, under these conditions, several different reaction pathways, including direct carbene N-H insertion, are possible. The reaction is markedly affected by the N-protecting group, the substrate structure and solvent. For those diazo ketones derived from N-tosyl-protected β-amino acids, the diazo decomposition with anhydrous THF as solvent and PhCO2Ag dissolved in Et3N as catalyst gives the corresponding 5-substituted pyrrolidinones in excellent yields.
- Wang, Jianbo,Hou, Yihua
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p. 1919 - 1923
(2007/10/03)
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