Diastereoselective synthesis of 6-functionalized 4-aryl-1,3-oxazinan-2-ones and their application in the synthesis of 3-aryl-1,3-aminoalcohols and 6-arylpiperidine-2,4-diones

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Mangelinckx S., Nural Y., DÖNDAŞ H. A., Denolf B., Sillanpaa R., De Kimpe N.

TETRAHEDRON, cilt.66, sa.23, ss.4115-4124, 2010 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 66 Sayı: 23
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1016/j.tet.2010.03.113
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4115-4124
  • Anahtar Kelimeler: Cyclocarbamation, 1,3-Oxazinan-2-ones, 1,3-Aminoalcohols, Piperidine-2,4-diones, ASYMMETRIC TOTAL-SYNTHESIS, CHIRAL BUILDING-BLOCK, STEREOSELECTIVE-SYNTHESIS, ALPHA-AMINO, INTRAMOLECULAR AMIDOALKYLATION, STREPTOMYCES-CLAVULIGERUS, CONCISE SYNTHESIS, SPERABILLINS-B, ACID, ROUTE
  • Çukurova Üniversitesi Adresli: Hayır

Özet

Halocyclocarbamation of benzyl N-(1-phenyl-3-butenyl)carbamates afforded 6-functionalized 4-aryl-1,3-oxazinan-2-ones with moderate to excellent diastereoselectivity depending on the N-substituent. Importantly, in contrast to reported cyclocarbamations of homoallylic carbamates, which are generally trans-diastereoselective, cyclization of N-unsubstituted Cbz-protected homoallylamines led to cis-1,3-oxazinan-2-ones, predominantly. The use of N-benzylated and in situ prepared N-silylated derivatives resulted however in trans-selectivity. Transition states are proposed to explain the stereochemical influence of the N-substituent on the cyclocarbamations. The functionalized 1,3-oxazinan-2-ones could be further elaborated towards biologically or synthetically important 6-arylpiperidine-2,4-diones and 3-aryl-1,3-aminoalcohols. (C) 2010 Elsevier Ltd. All rights reserved.