Synthesis of 2-azaspiro[4.6]undec-7-enes from N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols.
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.
Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China. cheyeh@ntnu.edu.tw
Ming-Chang P
MC
Yeh
Chia-Jung
CJ
Liang
Chern-Wei
CW
Fan
Wei-Hang
WH
Chiu
Jun-Yuan
JY
Lo
D002384:Catalysis; D003500:Cyclization; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D003511:Cyclohexanols; D013141:Spiro Compounds; D014105:Tosyl Compounds