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A. K. Ghosh W. J. Thompson M. K. Holloway S. P. McKee T. T. Duong H. Y. Lee P. M. Munson A. M. Smith J. M. Wai P. L. Darke J. A. Zugay E. A. Emini W. A. Schleif J. R. Huff P. S. Anderson J. Med. Chem. 1993 36 2300
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We have found that α,β-aziridinoaldehydes decompose to give complex mixtures on storage; this instability might account for the low yields of 2 under Wittig and other methylenation conditions
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For reactions of lithiated 4d with 1,2-di-, 1,2,2-tri-, and symmetrical 1,2,3-trisubstituted aziridines, see:
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25
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0030880685
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For a demonstration of the effect of aziridine stereochemistry on the regioselectivity of ring-opening by organocopper reagents, see:
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H. Aoyama N. Mimura H. Ohno K. Ishii A. Toda H. Tamamura A. Otaka N. Fujii T. Ibuka Tetrahedron Lett. 1997 38 7383
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28
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0000364997
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Aziridine 10 has been synthesised in enantiomerically enriched form: see ref. 20. In the present work the mono-TBDMS derivative of Z-2-butene-1,4-diol 22 was subjected to Sharpless aziridination conditions (ref. 3) to provide (±)- 10 in 72% yield
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