Novel phosphine-catalyzed zipper cyclization of aliphatic diyne-dione and yne-dione systems

Organic Letters

Volumn 5, Issue 2, 2003, Pages 129-131

  Kuroda, Hirofumi ^a,b   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a,c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOYAMA NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^c YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC COMPOUND; BICYCLO COMPOUND; KETONE DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 0013286401     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020198n     Document Type: Article

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12. 1H COSY spectra. The carbon skeleton in the bicyclic system was supported by the INADEQUATE and HMBC techniques.
13. For example, the reaction of 1c provides 2c in 75% yield in the presence of benzyl alcohol.
14. +).
15. 1H NMR spectrum of 2a, two olefinic protons attributed to E- and Z-isomers were observed at 5.38 ppm (minor) and 5.44 ppm (major). For the determination of the stereochemistry of the products, the major isomer was reduced by DIBAL-H to the corresponding secondary alcohol. In the NOE differential experiment of the alcohol, an NOE was observed between the carbinol proton and the olefinic proton. Therefore, this major isomer was determined as a Z-isomer.
16. 13C NMR spectra of 2b and 2c, no peak assignable to diastereoisomers was observed.
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