Novel Thermal Reaction of Fischer Carbene Complexes with Imines: Synthesis of β-Methoxy Allylic Amine Derivatives

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3967-3969

  Sangu, Kenichiro ^b   Kagoshima, Hirotaka ^a,b   Fuchibe, Kohei ^b   Akiyama, Takahiko ^b  

^a IBARAKI UNIVERSITY   (Japan)

^b GAKUSHUIN UNIVERSITY   (Japan)

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ARTICLE;

EID: 0442268865     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026852g     Document Type: Article

References (34)

1. Fischer, E. O.; Maasböl, A. Angew. Chem., Int. Ed. Engl. 1964, 3, 580.
2. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 5, p 1065. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999; Chapter 2, p 13. (c) Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1. (d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.3, p 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.4, p 549. (h) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
3. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 5, p 1065. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999; Chapter 2, p 13. (c) Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1. (d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.3, p 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.4, p 549. (h) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
4. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 5, p 1065. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999; Chapter 2, p 13. (c) Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1. (d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.3, p 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.4, p 549. (h) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
5. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 5, p 1065. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999; Chapter 2, p 13. (c) Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1. (d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.3, p 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.4, p 549. (h) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
6. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 5, p 1065. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999; Chapter 2, p 13. (c) Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1. (d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.3, p 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.4, p 549. (h) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
7. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 5, p 1065. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999; Chapter 2, p 13. (c) Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1. (d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.3, p 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.4, p 549. (h) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
8. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 5, p 1065. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999; Chapter 2, p 13. (c) Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1. (d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.3, p 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.4, p 549. (h) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
9. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, Chapter 5, p 1065. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 1999; Chapter 2, p 13. (c) Brown, F. J. Prog. Inorg. Chem. 1980, 27, 1. (d) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (e) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.3, p 469. (f) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. (g) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, Chapter 5.4, p 549. (h) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
10. 1(20) synthesis, see: (a) Dötz, K. H.; Pruskil, I. J. Organomet. Chem. 1981, 209. C4. (b) Dötz, K. H.; Pruskil, I.; Mühlemeier, J. Chem. Ber. 1982, 115, 1278. For the (+)-tetrahydrocerulenin synthesis, see: (c) Miller, M.; Hegedus, L. S. J. Org. Chem. 1993, 58, 6779.
11. 1(20) synthesis, see: (a) Dötz, K. H.; Pruskil, I. J. Organomet. Chem. 1981, 209. C4. (b) Dötz, K. H.; Pruskil, I.; Mühlemeier, J. Chem. Ber. 1982, 115, 1278. For the (+)-tetrahydrocerulenin synthesis, see: (c) Miller, M.; Hegedus, L. S. J. Org. Chem. 1993, 58, 6779.
12. 1(20) synthesis, see: (a) Dötz, K. H.; Pruskil, I. J. Organomet. Chem. 1981, 209. C4. (b) Dötz, K. H.; Pruskil, I.; Mühlemeier, J. Chem. Ber. 1982, 115, 1278. For the (+)-tetrahydrocerulenin synthesis, see: (c) Miller, M.; Hegedus, L. S. J. Org. Chem. 1993, 58, 6779.
13. (a) Kagoshima, H.; Akiyama, T. J. Am. Chem. Soc. 2000, 122, 11741.
14. (b) Kagoshima, H.; Okamura, T.; Akiyama, T. J. Am. Chem. Soc. 2001, 123, 7182.
15. Thermal reactions of carbene complexes with imines have been examined by other groups. For reactions of acyloxy and alkoxy carbene complexes with imines, see: (a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142. For cyclizations of the carbene complexes with α,β-unsaturated imines, see: (b) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443. (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; López-Ortiz, F. J. Chem. Soc., Chem. Commun. 1994, 321. (d) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 665. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695. (f) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996, 2, 88. (g) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229. (h) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065 and references therein.
16. Thermal reactions of carbene complexes with imines have been examined by other groups. For reactions of acyloxy and alkoxy carbene complexes with imines, see: (a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142. For cyclizations of the carbene complexes with α,β-unsaturated imines, see: (b) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443. (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; López-Ortiz, F. J. Chem. Soc., Chem. Commun. 1994, 321. (d) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 665. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695. (f) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996, 2, 88. (g) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229. (h) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065 and references therein.
17. Thermal reactions of carbene complexes with imines have been examined by other groups. For reactions of acyloxy and alkoxy carbene complexes with imines, see: (a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142. For cyclizations of the carbene complexes with α,β-unsaturated imines, see: (b) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443. (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; López-Ortiz, F. J. Chem. Soc., Chem. Commun. 1994, 321. (d) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 665. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695. (f) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996, 2, 88. (g) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229. (h) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065 and references therein.
18. Thermal reactions of carbene complexes with imines have been examined by other groups. For reactions of acyloxy and alkoxy carbene complexes with imines, see: (a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142. For cyclizations of the carbene complexes with α,β-unsaturated imines, see: (b) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443. (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; López-Ortiz, F. J. Chem. Soc., Chem. Commun. 1994, 321. (d) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 665. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695. (f) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996, 2, 88. (g) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229. (h) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065 and references therein.
19. Thermal reactions of carbene complexes with imines have been examined by other groups. For reactions of acyloxy and alkoxy carbene complexes with imines, see: (a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142. For cyclizations of the carbene complexes with α,β-unsaturated imines, see: (b) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443. (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; López-Ortiz, F. J. Chem. Soc., Chem. Commun. 1994, 321. (d) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 665. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695. (f) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996, 2, 88. (g) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229. (h) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065 and references therein.
20. Thermal reactions of carbene complexes with imines have been examined by other groups. For reactions of acyloxy and alkoxy carbene complexes with imines, see: (a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142. For cyclizations of the carbene complexes with α,β-unsaturated imines, see: (b) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443. (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; López-Ortiz, F. J. Chem. Soc., Chem. Commun. 1994, 321. (d) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 665. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695. (f) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996, 2, 88. (g) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229. (h) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065 and references therein.
21. Thermal reactions of carbene complexes with imines have been examined by other groups. For reactions of acyloxy and alkoxy carbene complexes with imines, see: (a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142. For cyclizations of the carbene complexes with α,β-unsaturated imines, see: (b) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443. (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; López-Ortiz, F. J. Chem. Soc., Chem. Commun. 1994, 321. (d) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 665. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695. (f) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996, 2, 88. (g) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229. (h) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065 and references therein.
22. Thermal reactions of carbene complexes with imines have been examined by other groups. For reactions of acyloxy and alkoxy carbene complexes with imines, see: (a) Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142. For cyclizations of the carbene complexes with α,β-unsaturated imines, see: (b) Danks, T. N.; Velo-Rego, D. Tetrahedron Lett. 1994, 35, 9443. (c) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; López-Ortiz, F. J. Chem. Soc., Chem. Commun. 1994, 321. (d) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 665. (e) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695. (f) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Carbajo, R. J.; López-Ortiz, F.; García-Granda, S.; Pertierra, P. Chem. Eur. J. 1996, 2, 88. (g) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229. (h) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Priede, M. P. J. Am. Chem. Soc. 1999, 121, 3065 and references therein.
23. No identifiable products besides 3a were isolated.
24. N-Benzylideneaniline gave unsatisfactory results even in 1,2-dichloroethane solvent. Reaction of complex 1 and imine 2a in 1,2-dichloroethane took as much as 32 h to complete, and the yield of the product 3a was less than 10%.
25. In all of the cases listed in Table 1, the starting complex 1 had disappeared completely. No identifiable products other than the allylic amine products were isolated.
26. We were unable to recover the starling complex 1.
27. 6.
28. We suppose that the N-sulfonyl group promotes this coordination step because an electron-withdrawing group makes back-donation from metal to imine more facile.
29. We cannot exclude the following alternative mechanism: 10 undergoes reductive elimination to give an aziridine intermediate. The aziridine intermediate affords the β-methoxy allylic amine product by ring-opening reaction.
30. H. -U. Reissig and his co-worker described the same kind of mechanism for their insertion reaction of a carbene ligand into an olefinic C-H bond. See: Wienand, A.; Reissig, H.-U. Angew. Chem., Int. Ed. Engl. 1990, 29, 1129.
31. 3) to afford the β-methoxy allylic amine product 5a (23 mg, 73%).
32. We suppose that the products are stable under the reaction conditions. For example, when p-tolylimine 4e was heated with complex 1 for 24 h, the allylic amine derivative 5e was obtained in 68% yield.
33. Geometry of the carbon-carbon double bond was not determined.
34. It is supposed that irradiation of carbene complexes causes metal-to-ligand charge transfer, which promotes formation of ketene-chromium complexes (See ref 2h). On the other hand, we suppose that thermal dissociation of the carbonyl ligand takes place when the carbene complex is heated.