Catalytic enantioselective annulations via 1,4-addition - Aldol cyclization of functionalized organozinc reagents [9]

Journal of the American Chemical Society

Volumn 121, Issue 5, 1999, Pages 1104-1105

  Naasz, Robert ^a   Arnold, Leggy A ^a   Pineschi, Mauro ^a   Keller, Erik ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; BICYCLO COMPOUND; ORGANOMETALLIC COMPOUND; REAGENT; ZINC DERIVATIVE;

CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; LETTER; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0033540709     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983693g     Document Type: Letter

References (44)

1. For reviews see: (a) Jung, M. E. Tetrahedron 1976, 32, 1-31. (b) Gawley, R. E. Synthesis 1976, 777-794.
2. For reviews see: (a) Jung, M. E. Tetrahedron 1976, 32, 1-31. (b) Gawley, R. E. Synthesis 1976, 777-794.
3. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 59, 1615-1621.
4. Buchsacher, P.; Fürst, A. Org. Synth. 1984, 63, 37-43. For the [5,6]- bicyclo enedione 97% ee is obtained: Cohen, N. Acc. Chem. Res. 1976, 9, 412-417. Hajos, Z. G.; Parrish, D. R. Org. Synth. 1984, 63, 26-36.
5. Buchsacher, P.; Fürst, A. Org. Synth. 1984, 63, 37-43. For the [5,6]-bicyclo enedione 97% ee is obtained: Cohen, N. Acc. Chem. Res. 1976, 9, 412-417. Hajos, Z. G.; Parrish, D. R. Org. Synth. 1984, 63, 26-36.
6. Buchsacher, P.; Fürst, A. Org. Synth. 1984, 63, 37-43. For the [5,6]- bicyclo enedione 97% ee is obtained: Cohen, N. Acc. Chem. Res. 1976, 9, 412-417. Hajos, Z. G.; Parrish, D. R. Org. Synth. 1984, 63, 26-36.
7. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
8. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
9. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
10. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
11. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
12. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326-2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
13. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634-636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
14. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
15. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261-4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
16. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
17. For reviews of other (asymmetric) annulation methodology, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Annulation via the addition of allylsilanes: Schinzer, D. Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; p 2087. Catalytic annulation via [3+2] cycloaddition: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1-20. Binger, F.; Fox, D.; Methods of Organic Chemistry; Houben Weyl: Stuttgart, 1996; Vol. E21, p 3055. Cyclopentannulation: Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326- 2335. Huart, C.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 634- 636. Cycloisomerizations: Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. The enantioselective Diels-Alder reaction to (chiral) cycloalkenones to provide chiral decalines was extensively studied by Taticchi et al.: Minuti, L.; Radics, L.; Taticchi, A.; Venturini, L.; Wenkert, E. J. Org. Chem. 1990, 55, 4261- 4265 and references cited therein. Until now no catalytic enantioselective version of this reaction was known. (Catalytic) asymmetric conjugate addition of organometallic reagents: Feringa, B. L.; De Vries, A. H. M. Adv. Catal. Processes 1995, 1, 151. Bosshamer, S.; Gais, H.-J. Synthesis 1998, 919-927.
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31. 6,9 in toluene was added and the reaction mixture was stirred overnight at -30°C. Aqueous workup followed by column chromatography (silica, hexanes-ether: 3-1) yielded pure 4a as a colorless oil (462 mg, 1.9 mmol, 91%). Cyclization to 5a was performed according to a literature procedure: see ref 10b. Further details: see Supporting Information.
32. For 3-ethylcycloheptanone the ee was incorrectly reported to be 53% (see ref 6b).
33. The bicyclo[4.3.0]nonenone skeleton can be found in many natural products: Porter, L. A. Chem. Rev. 1967, 67, 441-464.
34. Keller, E.; Maurer, J.; Naasz, R.; Schrader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409-2413. Arnold, L. A.; Feringa, B. L. unpublished results.
35. Keller, E.; Maurer, J.; Naasz, R.; Schrader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409-2413. Arnold, L. A.; Feringa, B. L. unpublished results.
36. Pfaltz et al. recently reported up to 72% ee in the 1,4-addition to cyclopentenone: Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Synlett 1997, 1429-1431.
37. Kitamura, M.; Miki, T.; Nakano, K.; Noyori, R. Tetrahedron Lett. 1996, 37, 5141-5144.
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39. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985.
40. (c) Feringa, B. L. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
41. Procedures for related ring closures with KOH in water or ethanol at reflux yielded a mixture of three products: (a) Welch, S. C.; Asserq, J.-M.; Loh, J.-P. Tetrahedron Lett. 1986, 27, 1115-1118. (b) Islam, A. M.; Raphael, R. A. J. Chem. Soc. 1952, 4086-4087.
42. Procedures for related ring closures with KOH in water or ethanol at reflux yielded a mixture of three products: (a) Welch, S. C.; Asserq, J.-M.; Loh, J.-P. Tetrahedron Lett. 1986, 27, 1115-1118. (b) Islam, A. M.; Raphael, R. A. J. Chem. Soc. 1952, 4086-4087.
43. A trans:cis ratio of 35:1 was found after the Wacker oxidation which is due to slow conversion of the cis-isomer of 6a.
44. For a recent enantioselective synthesis of a bicyclo[4.3.0]nonenone skeleton, see: Mukai, C.; Kim, J. S.; Uchiyama, M.; Hanaoka, M. Tetrahedron Lett. 1998, 39, 7909-7912.