A novel tandem [2 + 2] cycloaddition-Dieckmann condensation: Facile one- pot process to obtain 2,3-disubstituted-2-cycloalkenones from ynolates [6]

Journal of the American Chemical Society

Volumn 121, Issue 27, 1999, Pages 6507-6508

  Shindo, Mitsuru ^a   Sato, Yusuke ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALICYCLIC HYDROCARBON; KETENE DERIVATIVE;

CATALYSIS; DECARBOXYLATION; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0033554048     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990656w     Document Type: Letter

References (25)

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6. Stepwise mechanism cannot be ruled out, but in this manuscript, [2 + 2] cycloaddition is used as a matter of convenience.
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15. A review for Dieckmann condensation: Davis, D. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991 ; Vol. 2, pp 795-863. Recent examples for tandem Michael addition-Dieckmann condensation: Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. Tetrahedron Lett. 1998,39, 1771-1772. Kobayashi, K.; Maeda, K.; Uneda, T.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans, 1, 1997, 443-446. Maiti, S.; Bhaduri, S.; Achari, B.; Banerjee, A. K.; Nayak, N. P.; Mukherjee, A. K. Tetrahedron Lett. 1996, 44, 8061-8062. Groth, U.; Halfgang, W.; Köhler, T.; Kreye, P. Liebigs Ann. Chem. 1994, 885-890. Honda, T.; Mori, M. Chem. Lett. 1994, 1013-1016. Periasamy, M.; Reddy, M. R.; Radhakrishnan, U.; Devasagayaraj, A. J. Org. Chem. 1993, 58, 4997- 4999. Bunce, R. A.; Harris, C. R. J. Org. Chem. 1992, 57, 6981-6985.
16. A review for Dieckmann condensation: Davis, D. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991 ; Vol. 2, pp 795-863. Recent examples for tandem Michael addition-Dieckmann condensation: Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. Tetrahedron Lett. 1998,39, 1771-1772. Kobayashi, K.; Maeda, K.; Uneda, T.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans, 1, 1997, 443-446. Maiti, S.; Bhaduri, S.; Achari, B.; Banerjee, A. K.; Nayak, N. P.; Mukherjee, A. K. Tetrahedron Lett. 1996, 44, 8061-8062. Groth, U.; Halfgang, W.; Köhler, T.; Kreye, P. Liebigs Ann. Chem. 1994, 885-890. Honda, T.; Mori, M. Chem. Lett. 1994, 1013-1016. Periasamy, M.; Reddy, M. R.; Radhakrishnan, U.; Devasagayaraj, A. J. Org. Chem. 1993, 58, 4997- 4999. Bunce, R. A.; Harris, C. R. J. Org. Chem. 1992, 57, 6981-6985.
17. A review for Dieckmann condensation: Davis, D. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991 ; Vol. 2, pp 795-863. Recent examples for tandem Michael addition-Dieckmann condensation: Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. Tetrahedron Lett. 1998,39, 1771-1772. Kobayashi, K.; Maeda, K.; Uneda, T.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans, 1, 1997, 443-446. Maiti, S.; Bhaduri, S.; Achari, B.; Banerjee, A. K.; Nayak, N. P.; Mukherjee, A. K. Tetrahedron Lett. 1996, 44, 8061-8062. Groth, U.; Halfgang, W.; Köhler, T.; Kreye, P. Liebigs Ann. Chem. 1994, 885-890. Honda, T.; Mori, M. Chem. Lett. 1994, 1013-1016. Periasamy, M.; Reddy, M. R.; Radhakrishnan, U.; Devasagayaraj, A. J. Org. Chem. 1993, 58, 4997- 4999. Bunce, R. A.; Harris, C. R. J. Org. Chem. 1992, 57, 6981-6985.
18. A review for Dieckmann condensation: Davis, D. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991 ; Vol. 2, pp 795-863. Recent examples for tandem Michael addition-Dieckmann condensation: Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. Tetrahedron Lett. 1998,39, 1771-1772. Kobayashi, K.; Maeda, K.; Uneda, T.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans, 1, 1997, 443-446. Maiti, S.; Bhaduri, S.; Achari, B.; Banerjee, A. K.; Nayak, N. P.; Mukherjee, A. K. Tetrahedron Lett. 1996, 44, 8061-8062. Groth, U.; Halfgang, W.; Köhler, T.; Kreye, P. Liebigs Ann. Chem. 1994, 885-890. Honda, T.; Mori, M. Chem. Lett. 1994, 1013-1016. Periasamy, M.; Reddy, M. R.; Radhakrishnan, U.; Devasagayaraj, A. J. Org. Chem. 1993, 58, 4997- 4999. Bunce, R. A.; Harris, C. R. J. Org. Chem. 1992, 57, 6981-6985.
19. A review for Dieckmann condensation: Davis, D. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991 ; Vol. 2, pp 795-863. Recent examples for tandem Michael addition-Dieckmann condensation: Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. Tetrahedron Lett. 1998,39, 1771-1772. Kobayashi, K.; Maeda, K.; Uneda, T.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans, 1, 1997, 443-446. Maiti, S.; Bhaduri, S.; Achari, B.; Banerjee, A. K.; Nayak, N. P.; Mukherjee, A. K. Tetrahedron Lett. 1996, 44, 8061-8062. Groth, U.; Halfgang, W.; Köhler, T.; Kreye, P. Liebigs Ann. Chem. 1994, 885-890. Honda, T.; Mori, M. Chem. Lett. 1994, 1013-1016. Periasamy, M.; Reddy, M. R.; Radhakrishnan, U.; Devasagayaraj, A. J. Org. Chem. 1993, 58, 4997- 4999. Bunce, R. A.; Harris, C. R. J. Org. Chem. 1992, 57, 6981-6985.
20. A review for Dieckmann condensation: Davis, D. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991 ; Vol. 2, pp 795-863. Recent examples for tandem Michael addition-Dieckmann condensation: Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. Tetrahedron Lett. 1998,39, 1771-1772. Kobayashi, K.; Maeda, K.; Uneda, T.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans, 1, 1997, 443-446. Maiti, S.; Bhaduri, S.; Achari, B.; Banerjee, A. K.; Nayak, N. P.; Mukherjee, A. K. Tetrahedron Lett. 1996, 44, 8061-8062. Groth, U.; Halfgang, W.; Köhler, T.; Kreye, P. Liebigs Ann. Chem. 1994, 885-890. Honda, T.; Mori, M. Chem. Lett. 1994, 1013-1016. Periasamy, M.; Reddy, M. R.; Radhakrishnan, U.; Devasagayaraj, A. J. Org. Chem. 1993, 58, 4997-4999. Bunce, R. A.; Harris, C. R. J. Org. Chem. 1992, 57, 6981-6985.
21. A review for Dieckmann condensation: Davis, D. R.; Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991 ; Vol. 2, pp 795-863. Recent examples for tandem Michael addition-Dieckmann condensation: Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. Tetrahedron Lett. 1998,39, 1771-1772. Kobayashi, K.; Maeda, K.; Uneda, T.; Morikawa, O.; Konishi, H. J. Chem. Soc., Perkin Trans, 1, 1997, 443-446. Maiti, S.; Bhaduri, S.; Achari, B.; Banerjee, A. K.; Nayak, N. P.; Mukherjee, A. K. Tetrahedron Lett. 1996, 44, 8061-8062. Groth, U.; Halfgang, W.; Köhler, T.; Kreye, P. Liebigs Ann. Chem. 1994, 885-890. Honda, T.; Mori, M. Chem. Lett. 1994, 1013-1016. Periasamy, M.; Reddy, M. R.; Radhakrishnan, U.; Devasagayaraj, A. J. Org. Chem. 1993, 58, 4997- 4999. Bunce, R. A.; Harris, C. R. J. Org. Chem. 1992, 57, 6981-6985.
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