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Regio- and Stereocontrolled Synthesis of (2R*,3R*,4R*)-3,4-Dichloro-1,2,3,4,5,8-hexahydronaphthalen-2-yl Acetate via Tandem SN2′ Reactions

✍ Scribed by Nurhan Horasan-Kishali; Ertan Sahin; Yunus Kara

Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
218 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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).

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