Palladium-Catalyzed Cyclization of Cyclopropyl-Substituted 1,6-Enynes to 5.7-Bicyclic Trienes or Monocyclic Trienes Depending upon the Leaving Group

Hye Mi Oh; So Hee Sim; Sang Ick Lee; Jisu Kim; Young Keun Chung

doi:10.1055/s-0031-1290465

Synlett, Table of Contents

Synlett 2012; 23(18): 2657-2662
DOI: 10.1055/s-0031-1290465

letter

Palladium-Catalyzed Cyclization of Cyclopropyl-Substituted 1,6-Enynes to 5.7-Bicyclic Trienes or Monocyclic Trienes Depending upon the Leaving Group

Authors

Hye Mi Oh

Intelligent Textile System Research Center and Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-474, Korea Fax: +82(2)8890310 Email: ykchung@snu.ac.kr
So Hee Sim

Intelligent Textile System Research Center and Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-474, Korea Fax: +82(2)8890310 Email: ykchung@snu.ac.kr
Sang Ick Lee

Intelligent Textile System Research Center and Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-474, Korea Fax: +82(2)8890310 Email: ykchung@snu.ac.kr
Jisu Kim

Intelligent Textile System Research Center and Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-474, Korea Fax: +82(2)8890310 Email: ykchung@snu.ac.kr
Young Keun Chung*

Intelligent Textile System Research Center and Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-474, Korea Fax: +82(2)8890310 Email: ykchung@snu.ac.kr

Abstract

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Abstract

Palladium-catalyzed cyclization of cyclopropyl-substituted 1,6-enynes proceeded in two ways depending on the presence or absence of a leaving group. In the presence of the leaving group, 5.7-bicyclic trienes were obtained as the sole products; in the absence of the leaving group, monocyclic trienes were isolated.

Key words

palladium - enynes - vinyl cyclopropanes - seven-membered rings - bicyclic compounds

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References

References and Notes

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8 Spectroscopic Data for 1a: ¹H NMR (300 MHz, CDCl₃): δ = 7.75 (d, J = 8.1 Hz, 2 H), 7.33 (d, J = 8.0 Hz, 2 H), 6.02 (dd, J = 5.4, 11.1 Hz, 1 H), 5.67 (d, J = 11.0 Hz, 1 H), 4.84 (s, 1 H), 4.73 (s, 1 H), 4.34 (d, J = 3.4 Hz, 2 H), 4.21 (d, J = 3.3 Hz, 2 H), 2.43 (s, 5 H), 2.31 (t, J = 7.3 Hz, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 143.6, 142.6, 136.8, 134.0, 132.1, 130.7, 129.9, 127.6, 121.9, 114.3, 58.8, 56.8, 34.0, 28.5, 21.6. HRMS (EI): m/z [M]⁺ Calcd for C₁₇H₁₉NO₂S: 301.1137; found: 301.1142.
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