Substituent effects in the reaction of allyl trichloroacetimidates with N-halosuccinimides: Cyclization vs aza-Claisen rearrangement.

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1465-1468

  Shabany, Hossein ^a   Spilling, Christopher D ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; SUCCINIMIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION;

EID: 0032546257     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10837-1     Document Type: Article

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38. 2. The Z allylic hydroxyphosphonate 4h was prepared by Lindlar reduction of the corresponding propargylic hydroxy phosphonate and was reacted as described to give the imidate 5h. All new compounds were characterized by IR and NMR spectroscopy and elemental analysis, 1-cyano-3-phenyl-2-propenol, Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron Asymm. 1996, 7, 851; hydroxy propargylic phosphonates, Benayoud, F.; deMendonca, D. J.; Digits, C.A.; Moniz, G.A.; Sanders, T.C.; Hammond, G. B. J. Org. Chem. 1996, 61, 5159.
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43. 3 gave only the E amide 8a with 60% e.e.