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J Org Chem ; 77(21): 9707-17, 2012 Nov 02.
Article in English | MEDLINE | ID: mdl-23075326

ABSTRACT

The FeCl(3)-promoted synthesis of 2-azaspiro[4.6]undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.


Subject(s)
Cyclohexanols/chemistry , Cyclohexanols/chemical synthesis , Spiro Compounds/chemistry , Spiro Compounds/chemical synthesis , Tosyl Compounds/chemistry , Tosyl Compounds/chemical synthesis , Catalysis , Cyclization , Molecular Structure , Stereoisomerism
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