Torquoselectivity in the Cationic Cyclopentannelation of (2Z)-Hexa-2,4,5-trienal Acetals

Chemistry - A European Journal

Volumn 6, Issue 21, 2000, Pages 4021-4033

  Iglesias, Beatriz ^a   De Lera, Angel R ^a   Rodríguez Otero, Jesús ^b   López, Susana ^b  

^a UNIVERSITY OF VIGO   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Ab initio calculations; Acetals; Cyclizations; Hexa 2,4,5 trienal acetals; Selectivity

Indexed keywords

ACETAL DERIVATIVE; CYCLOPENTANE; HEXA 2,4,5 TRIENAL ACETAL DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; STEREOCHEMISTRY;

EID: 0034602087     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20001103)6:21<4021::AID-CHEM4021>3.3.CO;2-E     Document Type: Article

References (87)

1. A. R. de Lera, J. García Rey, D. A. Hrovat, B. Iglesias, S. López, Tetrahedron Lett. 1997, 38, 7425-7428.
2. [2f,g] c) interrupted Nazarov: J. A. Bender, A. E. Blize, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431; d) A. Pawda, T. M. Heidelbaugh, J. T. Kuether, M. S. McClure, J. Org. Chem. 1998, 63, 6778-6779; e) reductive Nazarov: S. Giese, F. G. West, Tetrahedron Lett. 1998, 39, 8393-8396; f) trapping of the oxyallyl intermediate: Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877; g) J. A. Bender, A.M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444.
3. [2f,g] c) interrupted Nazarov: J. A. Bender, A. E. Blize, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431; d) A. Pawda, T. M. Heidelbaugh, J. T. Kuether, M. S. McClure, J. Org. Chem. 1998, 63, 6778-6779; e) reductive Nazarov: S. Giese, F. G. West, Tetrahedron Lett. 1998, 39, 8393-8396; f) trapping of the oxyallyl intermediate: Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877; g) J. A. Bender, A.M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444.
4. [2f,g] c) interrupted Nazarov: J. A. Bender, A. E. Blize, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431; d) A. Pawda, T. M. Heidelbaugh, J. T. Kuether, M. S. McClure, J. Org. Chem. 1998, 63, 6778-6779; e) reductive Nazarov: S. Giese, F. G. West, Tetrahedron Lett. 1998, 39, 8393-8396; f) trapping of the oxyallyl intermediate: Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877; g) J. A. Bender, A.M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444.
5. [2f,g] c) interrupted Nazarov: J. A. Bender, A. E. Blize, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431; d) A. Pawda, T. M. Heidelbaugh, J. T. Kuether, M. S. McClure, J. Org. Chem. 1998, 63, 6778-6779; e) reductive Nazarov: S. Giese, F. G. West, Tetrahedron Lett. 1998, 39, 8393-8396; f) trapping of the oxyallyl intermediate: Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877; g) J. A. Bender, A.M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444.
6. [2f,g] c) interrupted Nazarov: J. A. Bender, A. E. Blize, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431; d) A. Pawda, T. M. Heidelbaugh, J. T. Kuether, M. S. McClure, J. Org. Chem. 1998, 63, 6778-6779; e) reductive Nazarov: S. Giese, F. G. West, Tetrahedron Lett. 1998, 39, 8393-8396; f) trapping of the oxyallyl intermediate: Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877; g) J. A. Bender, A.M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444.
7. [2f,g] c) interrupted Nazarov: J. A. Bender, A. E. Blize, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431; d) A. Pawda, T. M. Heidelbaugh, J. T. Kuether, M. S. McClure, J. Org. Chem. 1998, 63, 6778-6779; e) reductive Nazarov: S. Giese, F. G. West, Tetrahedron Lett. 1998, 39, 8393-8396; f) trapping of the oxyallyl intermediate: Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877; g) J. A. Bender, A.M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444.
8. [2f,g] c) interrupted Nazarov: J. A. Bender, A. E. Blize, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431; d) A. Pawda, T. M. Heidelbaugh, J. T. Kuether, M. S. McClure, J. Org. Chem. 1998, 63, 6778-6779; e) reductive Nazarov: S. Giese, F. G. West, Tetrahedron Lett. 1998, 39, 8393-8396; f) trapping of the oxyallyl intermediate: Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877; g) J. A. Bender, A.M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444.
9. For reviews, see: a) The Chemistry of Ketenes, Allenes and Related Compounds, Part II (Ed.: S. Patai), Wiley, New York, 1980; b) S. R. Landor, The Chemistry of the Allenes, Academic Press, New York, 1982; c) W. H. Okamura, Acc. Chem. Res. 1983, 16, 81-88; d) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley Interscience, New York, 1984; e) D. J. Pasto, Tetrahedron 1984, 40, 2805-2827; f) "Allenes and Cumulenes", C. Bruneau, P. Dixneuf, in Comprehensive Organic Functional Group Transformations, Vol. 1 (Eds.: A. R. Katritzky, O. Meth-Cohn, C. Rees, S. Roberts), Pergamon Press, Oxford, 1995, Chapter 1.20, pp. 953-995.
10. For reviews, see: a) The Chemistry of Ketenes, Allenes and Related Compounds, Part II (Ed.: S. Patai), Wiley, New York, 1980; b) S. R. Landor, The Chemistry of the Allenes, Academic Press, New York, 1982; c) W. H. Okamura, Acc. Chem. Res. 1983, 16, 81-88; d) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley Interscience, New York, 1984; e) D. J. Pasto, Tetrahedron 1984, 40, 2805-2827; f) "Allenes and Cumulenes", C. Bruneau, P. Dixneuf, in Comprehensive Organic Functional Group Transformations, Vol. 1 (Eds.: A. R. Katritzky, O. Meth-Cohn, C. Rees, S. Roberts), Pergamon Press, Oxford, 1995, Chapter 1.20, pp. 953-995.
11. For reviews, see: a) The Chemistry of Ketenes, Allenes and Related Compounds, Part II (Ed.: S. Patai), Wiley, New York, 1980; b) S. R. Landor, The Chemistry of the Allenes, Academic Press, New York, 1982; c) W. H. Okamura, Acc. Chem. Res. 1983, 16, 81-88; d) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley Interscience, New York, 1984; e) D. J. Pasto, Tetrahedron 1984, 40, 2805-2827; f) "Allenes and Cumulenes", C. Bruneau, P. Dixneuf, in Comprehensive Organic Functional Group Transformations, Vol. 1 (Eds.: A. R. Katritzky, O. Meth-Cohn, C. Rees, S. Roberts), Pergamon Press, Oxford, 1995, Chapter 1.20, pp. 953-995.
12. For reviews, see: a) The Chemistry of Ketenes, Allenes and Related Compounds, Part II (Ed.: S. Patai), Wiley, New York, 1980; b) S. R. Landor, The Chemistry of the Allenes, Academic Press, New York, 1982; c) W. H. Okamura, Acc. Chem. Res. 1983, 16, 81-88; d) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley Interscience, New York, 1984; e) D. J. Pasto, Tetrahedron 1984, 40, 2805-2827; f) "Allenes and Cumulenes", C. Bruneau, P. Dixneuf, in Comprehensive Organic Functional Group Transformations, Vol. 1 (Eds.: A. R. Katritzky, O. Meth-Cohn, C. Rees, S. Roberts), Pergamon Press, Oxford, 1995, Chapter 1.20, pp. 953-995.
13. For reviews, see: a) The Chemistry of Ketenes, Allenes and Related Compounds, Part II (Ed.: S. Patai), Wiley, New York, 1980; b) S. R. Landor, The Chemistry of the Allenes, Academic Press, New York, 1982; c) W. H. Okamura, Acc. Chem. Res. 1983, 16, 81-88; d) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley Interscience, New York, 1984; e) D. J. Pasto, Tetrahedron 1984, 40, 2805-2827; f) "Allenes and Cumulenes", C. Bruneau, P. Dixneuf, in Comprehensive Organic Functional Group Transformations, Vol. 1 (Eds.: A. R. Katritzky, O. Meth-Cohn, C. Rees, S. Roberts), Pergamon Press, Oxford, 1995, Chapter 1.20, pp. 953-995.
14. For reviews, see: a) The Chemistry of Ketenes, Allenes and Related Compounds, Part II (Ed.: S. Patai), Wiley, New York, 1980; b) S. R. Landor, The Chemistry of the Allenes, Academic Press, New York, 1982; c) W. H. Okamura, Acc. Chem. Res. 1983, 16, 81-88; d) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley Interscience, New York, 1984; e) D. J. Pasto, Tetrahedron 1984, 40, 2805-2827; f) "Allenes and Cumulenes", C. Bruneau, P. Dixneuf, in Comprehensive Organic Functional Group Transformations, Vol. 1 (Eds.: A. R. Katritzky, O. Meth-Cohn, C. Rees, S. Roberts), Pergamon Press, Oxford, 1995, Chapter 1.20, pp. 953-995.
15. For recent studies of the "allene effect" in pericyclic reactions, see: a) T. M. Morwick, L. A. Paquette, J. Org. Chem. 1997, 62, 627-635; b) F. Jensen, J. Am. Chem. Soc. 1995, 117, 7487-7492; c) E. Vedejs, A. Cammers-Goodwin, J. Org. Chem. 1994, 59, 7541-7543.
16. For recent studies of the "allene effect" in pericyclic reactions, see: a) T. M. Morwick, L. A. Paquette, J. Org. Chem. 1997, 62, 627-635; b) F. Jensen, J. Am. Chem. Soc. 1995, 117, 7487-7492; c) E. Vedejs, A. Cammers-Goodwin, J. Org. Chem. 1994, 59, 7541-7543.
17. For recent studies of the "allene effect" in pericyclic reactions, see: a) T. M. Morwick, L. A. Paquette, J. Org. Chem. 1997, 62, 627-635; b) F. Jensen, J. Am. Chem. Soc. 1995, 117, 7487-7492; c) E. Vedejs, A. Cammers-Goodwin, J. Org. Chem. 1994, 59, 7541-7543.
18. Although the rearrangement of the parent allenylvinylketone to alkylidenecyclopentenone has yet to be described, a recent report has shown that cyclization of highly substituted allenylvinylketones to the corresponding alkylidenecyclopentenones is indeed facile: A. S. K. Hashmi, J. W. Bats, J.-H. Choi, L. Schwarz, Tetrahedron Lett. 1998, 39, 7491-7494.
19. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
20. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
21. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
22. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
23. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
24. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
25. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
26. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
27. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
28. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
29. Other schemes for building the final cyclopentenone by in situ modification of allene precursors have been published: a) cyclization following ring opening of 1-vinylallene oxides generated upon epoxidation of vinylallenes (see refs. [6a-g]), and b) the analogous metal-assisted cyclization, which presumably involves the formation of a 2-cyclometallated vinylallene (see refs. [6h-k]). a) J. Grimaldi, M. Bertrand, Tetrahedron Lett. 1969, 3269-3272; b) M. Bertrand, J. P. Dulcere, G. Gil, Tetrahedron Lett. 1977, 4403-4406; c) M. Malacria, M. L. Roumestant, Tetrahedron 1977, 33, 2813-2817; d) M. Malacria, J. Gore, J. Org. Chem. 1979, 44, 885-886; e) A. Doutheau, J. Gore, J. Diab, Tetrahedron 1985, 41, 329-338; f) E. J. Corey, K. Ritter, M. Yus, C. Nájera, Tetrahedron Lett. 1987, 28, 3547-3550; g) S. W. Baertschi, A. R. Brash, T. M. Harris, J. Am. Chem. Soc. 1989, 111, 5003-5005; h) F. Delbecq, F. Gore, Tetrahedron Lett. 1976, 3459-3460; i) R. Baudouy, F. Delbecq, F. Gore, Tetrahedron 1980, 36, 189-195; j) R. Baudouy, J. Sartorelli, F. Choplin, Tetrahedron 1983, 39, 3293-3305; see also: k) V. Rautenstrauch, J. Org. Chem. 1984, 49, 8950-8952.
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