Regio- and stereocontrolled synthesis of (2R*,3R*,4R*)-3,4-dichloro-1,2,3,4,5,8-hexahydronaphthalen-2-yl acetate via tandem S(N)2 ' reactions

Horasan-Kishali N., Sahin E., Kara Y.

HELVETICA CHIMICA ACTA, cilt.89, sa.6, ss.1246-1253, 2006 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 89 Sayı: 6
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1002/hlca.200690122
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1246-1253
  • Atatürk Üniversitesi Adresli: Evet

Özet

The hydroperoxy endoperoxide 3, obtained by photooxygenation of isotetralin (= 1,4,5,8-tetrahydronaphthalene; 1), was reduced with thiourea, and the resulting intermediate 4 was converted, after acetylation with acetyl chloride, to the interesting, double-chlorinated acetate 5 in an unprecedented tandem reaction (Scheme 1). The structures and relative configurations of 3 and 5 were determined by NMR spectroscopy and by single-crystal X-ray-diffraction analyses (Figs. 1 and 2, resp.). A mechanistic rationalization for the conversion of 4 to 5 is proposed (Scheme 2).