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Regio‐ and Stereocontrolled Synthesis of (2 R* ,3 R* ,4 R* )‐3,4‐Dichloro‐1,2,3,4,5,8‐hexahydronaphthalen‐2‐yl Acetate via Tandem S N 2′ Reactions
Author(s) -
HorasanKishali Nurhan,
Sahin Ertan,
Kara Yunus
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690122
Subject(s) - chemistry , photooxygenation , thiourea , acetylation , tandem , chloride , single crystal , stereochemistry , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , crystallography , singlet oxygen , biochemistry , materials science , oxygen , composite material , gene
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 ).