Efficient Synthesis of Chiral Isoquinoline and Pyrido[1,2-b]-isoquinoline Derivatives via Intramolecular Heck Reactions

Advanced Synthesis and Catalysis

Volumn 343, Issue 4, 2001, Pages 360-368

  Sánchez Sancho, Francisco ^a   Mann, Enrique ^a   Herradón, Bernardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Biaryls; Intramolecular Heck reaction; Isoquinolines; Palladium; Pyrido 1,2 b isoquinolines

Indexed keywords

EID: 0042500332     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010430)343:4<360::AID-ADSC360>3.0.CO;2-2     Document Type: Article

References (86)

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9. For recent references on the synthesis of chiral partially reduced isoquinolines, see: (a) D. Taniyama, M. Hasegawa, K. Tomioka, Tetrahedron: Asymmetry 1999, 10, 221-223; (b) B. Wünsch, S. Nerdinger, Eur. J. Org. Chem. 1999, 503-517; (c) R. Yamaguchi, M. Tanaka, T. Matsuda, K. Fujita, Chem. Commun. 1999, 2213-2214; (d) F. A. Davis, Y. W. Andemichael, J. Org. Chem. 1999, 64, 8627-8634.
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11. For recent references on the synthesis of chiral partially reduced isoquinolines, see: (a) D. Taniyama, M. Hasegawa, K. Tomioka, Tetrahedron: Asymmetry 1999, 10, 221-223; (b) B. Wünsch, S. Nerdinger, Eur. J. Org. Chem. 1999, 503-517; (c) R. Yamaguchi, M. Tanaka, T. Matsuda, K. Fujita, Chem. Commun. 1999, 2213-2214; (d) F. A. Davis, Y. W. Andemichael, J. Org. Chem. 1999, 64, 8627-8634.
12. For recent references on the synthesis of chiral partially reduced pyrido[1,2-b]isoquinolines, see: (a) P. Lienard, J. Royer, J.-C. Quirion, H.-P. Husson, Tetrahedron Lett. 1991, 32, 2489-2492; (b) S. Lebrun, A. Couture, E. Deniau, P. Grandclaudon, Eur. J. Org. Chem. 1999, 2345-2352.
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14. For a comprehensive review on the synthesis of polyannular heterocycles, see: G. P. Ellis, Synthesis of Fused Heterocycles, John Wiley and Sons, Chichester, 1992.
15. F. Sánchez-Sancho, PhD thesis, Universidad Autónoma de Madrid, Spain, 1999.
16. E. Mann, F. Sánchez-Sancho, B. Herradón, to be submitted for publication.
17. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
18. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
19. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
20. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
21. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
22. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
23. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
24. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
25. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
26. For reviews on some aspects of the Heck reaction, see: (a) R. F. Heck, Organic Reactions 1982, 27, 345-390; (b) R. F. Heck, in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1991, pp 833-863; (c) A. de Meijere, F. E. Meyer, Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411; (d) A. Heumann, M. Réglier, Tetrahedron 1996, 52, 9289-9346; (e) S. E. Gibson, R. J. Middlenton, Contemp. Org. Synth. 1996, 3, 447-471; (f) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron 1997, 53, 7371-7395; (g) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427-436; (h) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066; (i) A. Yamamoto, Y. Kayaki, K. Nagayama, I. Shimizu, Synlett 2000, 925-937; (j) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321; (k) For a recent review on carbon-carbon bond formation (including Heck reaction) on solid phase, see: B. A. Lorsbach, M. J. Kurth, Chem. Rev. 1999, 99, 1549-1581.
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48. The reactions can be carried out in multigram scale, and all the intermediates can be purified by crystallization.
49. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
50. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
51. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
52. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
53. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
54. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
55. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
56. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
57. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
58. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
59. For some references, see: (a) R. Grigg, V. Loganathan, V. Santhakumar, V. Sridharan, A. Teasdale, Tetrahedron Lett. 1991, 32, 687-690; (b) R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, A. W. Bridge, Tetrahedron 1993, 49, 5177-5188; (c) T. Hudlicky, H. F. Olivo, B. McKibben, J. Am. Chem. Soc. 1994, 116, 5108-5115; (d) S. E. Denmark, M. E. Schnute, J. Org. Chem. 1995, 60, 1013-1019; (e) D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett 1996, 1091-1092; (f) T. Ohshima, K. Kagechika, M. Adachi, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1996, 118, 7108-7116; (g) L. E. Overman, D. J. Poon, Angew. Chem. Int. Ed. Engl. 1997, 36, 518-521; (h) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; (i) V. B. Birman, V. H. Rawal, Tetrahedron Lett. 1998, 39, 7219-222; (j) S. E. Gibson (née Thomas), J. O. Jones, R. McCague, M. J. Tozer, N. J. Whitcombe, Synlett 1999, 954-956; (k) J. Priego, J. C. Carretero, Synlett 1999, 1603-1605.
60. T. Jeffery, Tetrahedron 1996, 52, 10113-10130, and references cited therein.
61. For recent reports on the Heck reaction in the presence of tetraalkylammonium salts, see: (a) S. E. Gibson (née Thomas), N. Guillo, R. J. Middleton, A. Thuilliez, M. J. Tozer, J. Chem. Soc., Perkin Trans 1, 1997, 447-455; (b) R. C. Larock, P. Pace, H. Yang, C. E. Russell, S. Cacchi, G. Fabrizi, Tetrahedron 1998, 54, 9961-9980; (c) R. C. Larock, X. Han, J. Org. Chem. 1999, 64, 1875-1887.
62. For recent reports on the Heck reaction in the presence of tetraalkylammonium salts, see: (a) S. E. Gibson (née Thomas), N. Guillo, R. J. Middleton, A. Thuilliez, M. J. Tozer, J. Chem. Soc., Perkin Trans 1, 1997, 447-455; (b) R. C. Larock, P. Pace, H. Yang, C. E. Russell, S. Cacchi, G. Fabrizi, Tetrahedron 1998, 54, 9961-9980; (c) R. C. Larock, X. Han, J. Org. Chem. 1999, 64, 1875-1887.
63. For recent reports on the Heck reaction in the presence of tetraalkylammonium salts, see: (a) S. E. Gibson (née Thomas), N. Guillo, R. J. Middleton, A. Thuilliez, M. J. Tozer, J. Chem. Soc., Perkin Trans 1, 1997, 447-455; (b) R. C. Larock, P. Pace, H. Yang, C. E. Russell, S. Cacchi, G. Fabrizi, Tetrahedron 1998, 54, 9961-9980; (c) R. C. Larock, X. Han, J. Org. Chem. 1999, 64, 1875-1887.
64. M. M. Abelman, T. Oh, L. E. Overman, J. Org. Chem. 1987, 52, 4130-4133.
65. For recent reports on the Heck reaction in the presence of silver(I) salts, see: (a) L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schuberth, Angew. Chem. Int. Ed. Engl. 1996, 35, 2674-2677; (b) F. Miyazaki, K. Uotsu, M. Shibasaki, Tetrahedron 1998, 54, 13075-13078; (c) S. Honzawa, T. Mizutani, M. Shibasaki, Tetrahedron Lett. 1999, 40, 311-314; (d) M. M. Segorbe, J. Adrio, J. C. Carretero, Tetrahedron Lett. 2000, 41, 1983-1986.
66. For recent reports on the Heck reaction in the presence of silver(I) salts, see: (a) L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schuberth, Angew. Chem. Int. Ed. Engl. 1996, 35, 2674-2677; (b) F. Miyazaki, K. Uotsu, M. Shibasaki, Tetrahedron 1998, 54, 13075-13078; (c) S. Honzawa, T. Mizutani, M. Shibasaki, Tetrahedron Lett. 1999, 40, 311-314; (d) M. M. Segorbe, J. Adrio, J. C. Carretero, Tetrahedron Lett. 2000, 41, 1983-1986.
67. For recent reports on the Heck reaction in the presence of silver(I) salts, see: (a) L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schuberth, Angew. Chem. Int. Ed. Engl. 1996, 35, 2674-2677; (b) F. Miyazaki, K. Uotsu, M. Shibasaki, Tetrahedron 1998, 54, 13075-13078; (c) S. Honzawa, T. Mizutani, M. Shibasaki, Tetrahedron Lett. 1999, 40, 311-314; (d) M. M. Segorbe, J. Adrio, J. C. Carretero, Tetrahedron Lett. 2000, 41, 1983-1986.
68. For recent reports on the Heck reaction in the presence of silver(I) salts, see: (a) L. F. Tietze, R. Hannemann, W. Buhr, M. Lögers, P. Menningen, M. Lieb, D. Starck, T. Grote, A. Döring, I. Schuberth, Angew. Chem. Int. Ed. Engl. 1996, 35, 2674-2677; (b) F. Miyazaki, K. Uotsu, M. Shibasaki, Tetrahedron 1998, 54, 13075-13078; (c) S. Honzawa, T. Mizutani, M. Shibasaki, Tetrahedron Lett. 1999, 40, 311-314; (d) M. M. Segorbe, J. Adrio, J. C. Carretero, Tetrahedron Lett. 2000, 41, 1983-1986.
69. [30,31] have been scarcely studied.
70. J. Hassan, V. Penalva, L. Lavenot, C. Gozzi, M. Lemaire, Tetrahedron 1998, 54, 13793-13804.
71. D. D. Hennings, T. Iwama, V. H. Rawal, Org. Lett. 1999, 1, 1205-1208.
72. Compounds of type 6 are potential inhibitors of HIV protease, see: M. T. Reetz, C. Merk, G. Mehler, Chem. Commun. 1998, 2075-2076.
73. Biaryl-substituted peptidomimetics with hydrophobic side-chains can have liquid crystal behavior; for a book treating different aspects of liquid crystals, see: P. J. Collings, Liquid Crystals. Nature's Delicate Phase of Matter, Adam Hilger, Bristol, 1990.
74. 4NI (1.1 mol equiv)/DMF/60°C] is extremely slow, reaching a 10% conversion after 36 hours.
75. For a recent review on the application of the Heck reaction in the synthesis of polyannular nitrogenated-heterocycles, see: M. Ikeda, S. A. A. El Bialy, T. Yakura, Heterocycles 1999, 51, 1957-1970.
76. (a) The Z-stereochemistry at the exocyclic double bond was assigned on basis to the existence of NOEs between the olefinic and H-5 protons in the NOESY spectra of compounds 5, and latter confirmed by single-crystal X-ray diffraction analysis of a derivative of 5b (E. Mann, F. Sánchez-Sancho, A. Chana, J. Mahía, M. A. Maestro, B. Herradón, unpublished observations).
77. [8]
78. [12,14b]
79. 1H NMR spectra; this shielding seems to indicate an interaction between the amide proton of 5c and the aromatic ring, that might contribute to an increased acidity of the allylic proton in either 4c or 5c (or in both, or in some of the intermediate of the Heck cyclization). For a thorough discussion on the interaction between hydrogen and aromatic compounds, see: G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999;
80. (b) An alternative strategy for the synthesis of enantiomerically pure 5c is through a lipase-catalyzed hydrolysis of racemic 5c (planned work).
81. M. Ors, A. Morcuende, M. I Jiménez-Vacas, S. Valverde, B. Herradón, Synlett 1996, 449-451.
82. [7,8] confirms that the overall transformation of (S)-7 into (S)-10 proceeded without racemization. (c) We did not detect any biaryl compound in these reactions.
83. F. Sánchez-Sancho, E. Mann, B. Herradón, Synlett 2000, 509-513.
84. (a) The synthesis of 12 was carried out in the racemic series. (b) Only starting material (> 95% yield) was recovered in the Heck reaction under Overman's conditions.
85. C. Gürtler, S. L. Buchwald, Chem. Eur. J. 1999, 5, 3107-3112, and references cited therein.
86. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.