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J Org Chem. 2012 Nov 2;77(21):9707-17. doi: 10.1021/jo301764g. Epub 2012 Oct 25.

Synthesis of 2-azaspiro[4.6]undec-7-enes from N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols.

Author information

1
Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China. cheyeh@ntnu.edu.tw

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.

PMID:
23075326
DOI:
10.1021/jo301764g
[Indexed for MEDLINE]

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