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
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).
Atıf için künye
Horasan, N., Şahin, E., & Kara, Y. (2006). 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. HELVETICA CHIMICA ACTA, 89(6), 1246–1253. https://doi.org/10.1002/hlca.200690122
BibTeX
@article{horasan2006-66563,
author = {Horasan, Nurhan and Şahin, Ertan and Kara, Yunus},
title = {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},
journal = {HELVETICA CHIMICA ACTA},
year = {2006},
volume = {89},
number = {6},
pages = {1246--1253},
issn = {0018-019X},
doi = {10.1002/hlca.200690122},
url = {https://akademik.atauni.edu.tr/yayinlar/66563-regio-and-stereocontrolled-synthesis-of-2r3r4r-34-dichloro-123458}
}