- Novel enantiomerically pure 2-amino-1,4-diols from chiral 4-hydroxymethyl-5-iodo-1,3-oxazin-2-ones
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Reduction of (4S,5S,6S)-4-hydroxymethyl-5-iodo-6-methyl-1,3-oxazin-2-one 2a and (4S,5S,6R)-4-hydroxymethyl-5-iodo-6-phenyl-1,3-oxazin-2-one 2b with tributyltin hydride in ethanol afforded 1,3-oxazin-2-one 3a and 1,3-oxazolidin-2-one 4b, respectively. Hydr
- Gonzalez-Rosende, M. Eugenia,Jorda-Gregori, J. Miquel,Sepulveda-Arques, Jose,Orena, Mario
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- Procedure-controlled enantioselectivity switch in organocatalytic 2-oxazolidinone synthesis
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In a novel organocatalytic formal [3 + 2] cycloaddition to afford chiral 2-oxazolidinones, an enantioselectivity switch could be induced by changing the manner of addition of the reactants, even when the reaction components (cinchona-alkaloid-derived aminothiourea catalyst, substrates, and solvent) were the same.
- Fukata, Yukihiro,Asano, Keisuke,Matsubara, Seijiro
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p. 12160 - 12163
(2013/09/23)
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- Preparation and reactivity of chiral β-amino-alkylzinc iodides and related configurationally stable zinc organometallics
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Several zinc organometallics bearing at the β-position a carbamate or an amido function with an acidic N-H group were prepared using the direct insertion of zinc dust into the corresponding alkyl iodides in THF or THF:DMSO mixtures. Most of the starting iodides were obtained from natural α-amino acids and the resulting zinc species afforded after transmetalation with CuCN.2LiCl and reaction with a selection of relatively reactive electrophiles a variety of polyfunctional 1,2-amino alcohol derivatives and carbamates in optically pure form. Several secondary β-amido alkyl iodides were converted to the corresponding chiral zinc reagents and trapped with electrophiles. The configurational stability of chiral secondary organozinc compounds and the stereochemical course of their reactions were examined.
- Duddu,Eckhardt,Furlong,Knoess,Berger,Knochel
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p. 2415 - 2432
(2007/10/02)
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