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For examples of intramolecular azidoformate C-H insertion reactions, see: (a) Berner, H.; Vyplel, H.; Schulz, G.; Stuchlik, P. Tetrahedron 1984, 40, 919. (b) Yuan, P.; Plourde, R.; Shoemaker, M. R.; Moore, C. L.; Hansen, D. E. J. Org. Chem. 1995, 60, 5360. (c) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Dawson, I. M.; Gosney, I.; Grant, K. J.; Gaur, S.; Hodgson, P. K. G.; Knight, K. S.; Smith, G. W.; Stevenson, D. E. Tetrahedron 1992, 48, 7979. For examples of intramolecular C=C insertion reactions of azidoformate-derived acyl nitrenes, see: (d) Rhouati, S.; Bernou, A. J. Chem. Soc., Chem. Commun. 1989, 730. (e) Bergmeier, S. C.; Stanchina, D. M. Tetrahedron Lett. 1995, 36, 4533. (f) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1997, 62, 4449.
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note
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Data resulting from the X-ray diffraction studies for crystals of compounds 5, 21, and 34b have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K. We acknowledge the collaborative efforts of J. C. Huffman, K. F. Streib, and W. C. Streib of the Indiana University Molecular Structure Center (Reports 93254, 93082, and 91057).
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-
-
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44
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0000478917
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-
Optically active dihydrofuran 30 was produced via reduction of (4S,5R)-4,5-dihydro-5-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2(3H)- furanone, which was prepared from D-glutamic acid following the literature for the enantiomeric butenolide. Hanessian, S.; Murray, P. J. J. Org. Chem. 1987, 52, 1170.
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0345400924
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Benzyl azidoformate was prepared following adaptation of the published procedure for ethyl azidoformate (ref 20).
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