- 1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams
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Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.
- Ishida, Naoki,Shimamoto, Yasuhiro,Yano, Takaaki,Murakami, Masahiro
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p. 19103 - 19106
(2014/01/17)
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- Regioselective cycloaddition of 3-azetidinones and 3-oxetanones with alkynes through nickel-catalysed carbon-carbon bond activation
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Get in the ring! The first examples of transition-metal-catalysed C-C bond activation of 3-azetidinones and 3-oxetanones are reported. In the presence of a nickel catalyst and alkynes, a regioselective and high-yielding [4+2] cycloaddition occurs, leading to the formation of pyridinones, pyranones and eventually 4,5-disubstituted 3-hydroxypyridines (see scheme). Copyright
- Ho, Kelvin Y. T.,Aissa, Christophe
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supporting information; experimental part
p. 3486 - 3489
(2012/05/19)
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- Reductive aldol and mannich-type reactions of azetidin-3-ones promoted by titanium tetraiodide
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A convenient method is described for the generation and reaction of the enolates of aminoacetone equivalents, which uses the reduction of azetidin-3-one with titanium tetraiodide and subsequent reactions with electrophiles. This methodology provides a str
- Hata, Shingo,Fukuda, Daisuke,Hachiya, Iwao,Shimizu, Makoto
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supporting information; experimental part
p. 473 - 477
(2010/08/23)
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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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- Antitumor agents: diazomethyl ketone and chloromethyl ketone analogues prepared from N-tosyl amino acids
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Diazomethyl ketone and chloromethyl ketone analogues prepared from N-tosyl amino acids have been synthesized and tested for antitumor activity in Ehrlich ascites carcinoma and P-388 lymphocytic leukemia screens in mice. The N-tosyl chloromethyl ketone ana
- Sajadi,Kashani,Loeffler,Hall
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p. 275 - 278
(2007/10/02)
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