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Hegedus has found that trialkylammonium salts can interfere with the diastereoselectivity of the Staudinger reaction to produce β-lactams:
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Hegedus has found that trialkylammonium salts can interfere with the diastereoselectivity of the Staudinger reaction to produce β-lactams:. Hegedus L.S., Montgomery J., Narukawa Y., and Snustad D.C. J. Am. Chem. Soc. 113 (1991) 5784-5791
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BEMP: 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazophosph orine.
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The product of the reaction between benzyl alcohol and the isocyanate produced from phenyl isopropyl ketene, which was obtained in 92% yield and 95% ee, was also reported.
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Many of the pharmaceutically relevant β-lactams are monosubstituted in the 3-position of the azetidin-2-one. One could foresee this moiety arising from the reaction of monosubstituted ketenes with imines.
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Molecular mechanics calculations confirm that there is a less than 0.5 kcal/mol difference between the diastereomeric acyl ammonium intermediates.
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