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 | Zendy

HorasanKishali Nurhan | Zendy; Sahin Ertan | Zendy; Kara Yunus | Zendy

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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 ).

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