An efficient synthesis of optically active trans-2-Aryl-2,3-dihydrobenzofuran-3-carboxylic acid esters via C-H insertion reaction

Synlett

Volumn , Issue 7, 2003, Pages 1028-1030

  Kurosawa, Wataru ^a   Kan, Toshiyuki ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

C H insertion; Chiral auxiliary; Dihydrobenzofuran; Pyrrolidinyl lactamide

Indexed keywords

AMIDE; AZO COMPOUND; CARBOXYLIC ACID DERIVATIVE; DIHYDROBENZOFURAN DERIVATIVE; ESTER DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CROSS LINKING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037805763     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39316     Document Type: Article

References (24)

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5. For construction of dihydrobenzofuran rings by oxidative dimerisation, see: (a) Rummakko, P.; Brunow, G.; Orlandi, M.; Rindone, B. Synlett 1999, 333. (b) Bolzacchini, E.; Brunow, G.; Meinardi, S.; Orlandi, M.; Rindone, B.; Rummakko, P.; Setala, H. Tetrahedron Lett. 1998, 39, 3291. (c) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2536. (d) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2500. (e) Antus, S.; Gottsegen, A.; Kolonits, P.; Wagner, H. Liebigs Ann. Chem. 1989, 593. (f) Antus, S.; Bauer, R.; Gottsegen, A.; Seligmann, O.; Wagner, H. Liebigs Ann. Chem. 1987, 357.
6. For construction of dihydrobenzofuran rings by oxidative dimerisation, see: (a) Rummakko, P.; Brunow, G.; Orlandi, M.; Rindone, B. Synlett 1999, 333. (b) Bolzacchini, E.; Brunow, G.; Meinardi, S.; Orlandi, M.; Rindone, B.; Rummakko, P.; Setala, H. Tetrahedron Lett. 1998, 39, 3291. (c) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2536. (d) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2500. (e) Antus, S.; Gottsegen, A.; Kolonits, P.; Wagner, H. Liebigs Ann. Chem. 1989, 593. (f) Antus, S.; Bauer, R.; Gottsegen, A.; Seligmann, O.; Wagner, H. Liebigs Ann. Chem. 1987, 357.
7. For construction of dihydrobenzofuran rings by oxidative dimerisation, see: (a) Rummakko, P.; Brunow, G.; Orlandi, M.; Rindone, B. Synlett 1999, 333. (b) Bolzacchini, E.; Brunow, G.; Meinardi, S.; Orlandi, M.; Rindone, B.; Rummakko, P.; Setala, H. Tetrahedron Lett. 1998, 39, 3291. (c) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2536. (d) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2500. (e) Antus, S.; Gottsegen, A.; Kolonits, P.; Wagner, H. Liebigs Ann. Chem. 1989, 593. (f) Antus, S.; Bauer, R.; Gottsegen, A.; Seligmann, O.; Wagner, H. Liebigs Ann. Chem. 1987, 357.
8. For construction of dihydrobenzofuran rings by oxidative dimerisation, see: (a) Rummakko, P.; Brunow, G.; Orlandi, M.; Rindone, B. Synlett 1999, 333. (b) Bolzacchini, E.; Brunow, G.; Meinardi, S.; Orlandi, M.; Rindone, B.; Rummakko, P.; Setala, H. Tetrahedron Lett. 1998, 39, 3291. (c) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2536. (d) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2500. (e) Antus, S.; Gottsegen, A.; Kolonits, P.; Wagner, H. Liebigs Ann. Chem. 1989, 593. (f) Antus, S.; Bauer, R.; Gottsegen, A.; Seligmann, O.; Wagner, H. Liebigs Ann. Chem. 1987, 357.
9. For construction of dihydrobenzofuran rings by oxidative dimerisation, see: (a) Rummakko, P.; Brunow, G.; Orlandi, M.; Rindone, B. Synlett 1999, 333. (b) Bolzacchini, E.; Brunow, G.; Meinardi, S.; Orlandi, M.; Rindone, B.; Rummakko, P.; Setala, H. Tetrahedron Lett. 1998, 39, 3291. (c) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2536. (d) Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2500. (e) Antus, S.; Gottsegen, A.; Kolonits, P.; Wagner, H. Liebigs Ann. Chem. 1989, 593. (f) Antus, S.; Bauer, R.; Gottsegen, A.; Seligmann, O.; Wagner, H. Liebigs Ann. Chem. 1987, 357.
10. For other methods for constructing dihydrohenzofuran rings, see: (a) Russell, M. G. N.; Baker, R.; Ball, R. G.; Thomas, S. R.; Tsou, N. N.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 2000, 893. (b) Russell, M. G. N.; Baker, R.; Castro, J. L. Tetrahedron Lett. 1999, 40, 8667. (c) Prakash, O.; Tanwar, M. P. Bull. Chem. Soc. Jpn. 1995, 68, 1168. (d) Baker, R.; Cooke, N. G.; Humphrey, G. R.; Wright, S. H. B.; Hirshfield, J. J. Chem. Soc., Chem. Commun. 1987, 1102.
11. For other methods for constructing dihydrohenzofuran rings, see: (a) Russell, M. G. N.; Baker, R.; Ball, R. G.; Thomas, S. R.; Tsou, N. N.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 2000, 893. (b) Russell, M. G. N.; Baker, R.; Castro, J. L. Tetrahedron Lett. 1999, 40, 8667. (c) Prakash, O.; Tanwar, M. P. Bull. Chem. Soc. Jpn. 1995, 68, 1168. (d) Baker, R.; Cooke, N. G.; Humphrey, G. R.; Wright, S. H. B.; Hirshfield, J. J. Chem. Soc., Chem. Commun. 1987, 1102.
12. For other methods for constructing dihydrohenzofuran rings, see: (a) Russell, M. G. N.; Baker, R.; Ball, R. G.; Thomas, S. R.; Tsou, N. N.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 2000, 893. (b) Russell, M. G. N.; Baker, R.; Castro, J. L. Tetrahedron Lett. 1999, 40, 8667. (c) Prakash, O.; Tanwar, M. P. Bull. Chem. Soc. Jpn. 1995, 68, 1168. (d) Baker, R.; Cooke, N. G.; Humphrey, G. R.; Wright, S. H. B.; Hirshfield, J. J. Chem. Soc., Chem. Commun. 1987, 1102.
13. For other methods for constructing dihydrohenzofuran rings, see: (a) Russell, M. G. N.; Baker, R.; Ball, R. G.; Thomas, S. R.; Tsou, N. N.; Castro, J. L. J. Chem. Soc., Perkin Trans. 1 2000, 893. (b) Russell, M. G. N.; Baker, R.; Castro, J. L. Tetrahedron Lett. 1999, 40, 8667. (c) Prakash, O.; Tanwar, M. P. Bull. Chem. Soc. Jpn. 1995, 68, 1168. (d) Baker, R.; Cooke, N. G.; Humphrey, G. R.; Wright, S. H. B.; Hirshfield, J. J. Chem. Soc., Chem. Commun. 1987, 1102.
14. For a review on asymmetric intermolecular C-H activation, see: Davies, H. M. L.; Antoulinakis, E. G. J. Organomet. Chem. 2001, 617, 47.
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17. 2.
18. Recently, Hashimoto reported a similar C-H insertion reaction with his Rh(II)-catalyst, which proceeded in high enantio- and diastereoselectivity: Treatment of a similar aryldiazoacetate with 1 mol% of the catalyst in toluene at -78°C provided the cis-benzofuran in 94% ee, see: Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Org. Lett. 2002, 4, 3887.
19. Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R. Jr.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468.
20. The high diastereoselectivities observed with 8b and 8c indicate that the carbenoid intermediate might have strong interaction with the carbonyl group of the chiral auxiliary as illustrated in Scheme 5. The similar interaction was reported in ref. 10.
21. N2 reaction of α-haloester derivatives, see: Devine, P. N.; Dolling, U.-H.; Heid, R. M. Jr.; Tschaen, D. M. Tetrahedron Lett. 1996, 37, 2683.
22. For double asymmetric induction in intramolecular C-H insertion reactions, see: Hashimoto, S.; Watanabe, N.; Kawano, K.; Ikegami, S. Synth. Commun. 1994, 24, 3277.
23. The absolute configuration of the major carboxylic acid was determined as (2R,3R) by comparison of the optical rotation of the corresponding methyl ester 9a with the related compound reported in ref. 5a. Furthermore, the dihydrobenzofuran 9a was independently synthesized by utilizing Evans' asymmetric aldol reaction and subsequent acidic cyclization to confirm the stereochemistry. For Evans' enantioselective aldol reaction, see: Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
24. We have recently completed the total synthesis of (-)-ephedradine A (4). Full details of the total synthesis of 4 will be reported in due course.