Unusual diastereoselection in the synthesis of nine-membered ring lactams and conformation-controlled transannular reactions to generate optically active indolizidinones

Angewandte Chemie - International Edition

Volumn 37, Issue 8, 1998, Pages 1140-1143

  Sudau, Alexander ^a   Nubbemeyer, Udo ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Chirality; Heterocycles; Lactams; Rearrangements; Ring contractions

Indexed keywords

EID: 0032482103     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1140::AID-ANIE1140>3.0.CO;2-W     Document Type: Article

References (35)

1. M. Diederich, U. Nubbemeyer, Angew. Chem. 1995, 107, 1095; Angew. Chem. Int. Ed. Engl. 1995, 34, 1026.
2. M. Diederich, U. Nubbemeyer, Angew. Chem. 1995, 107, 1095; Angew. Chem. Int. Ed. Engl. 1995, 34, 1026.
3. M. Diederich, U. Nubbemeyer, Chem. Eur. J. 1996, 2, 896.
4. Review on Claisen rearrangements: H. Frauenrath, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21 d, p. 3301.
5. L. F. Tietze, T. Eicher, Reaktionen und Synthesen im Organisch-Chemischen Praktikum, 2nd ed., Thieme, Stuttgart, 1991, p. 135.
6. R. N. Icke, B. B. Wisegarver, G. A. Alles, Org. Synth. Coll. Vol. 3 1955, 723; N-Methylproline methyl ester 2: R. L. Elliott, H. Kopeka, N.-H. Lin, Y. He, D. S. Garvey, Synthesis 1995, 772.
7. R. N. Icke, B. B. Wisegarver, G. A. Alles, Org. Synth. Coll. Vol. 3 1955, 723; N-Methylproline methyl ester 2: R. L. Elliott, H. Kopeka, N.-H. Lin, Y. He, D. S. Garvey, Synthesis 1995, 772.
8. L. F. Tietze, T. Eicher, Reaktionen und Synthesen im Organisch-Chemischen Praktikum, 2nd ed., Thieme, Stuttgart, 1991, p. 85; N-Benzylproline methyl ester 3: E. J. Corey, J. O. Link, J. Org. Chem. 1991, 56, 442.
9. L. F. Tietze, T. Eicher, Reaktionen und Synthesen im Organisch-Chemischen Praktikum, 2nd ed., Thieme, Stuttgart, 1991, p. 85; N-Benzylproline methyl ester 3: E. J. Corey, J. O. Link, J. Org. Chem. 1991, 56, 442.
10. E. J. Corey, A. Venkatesvarlu, J. Am. Chem. Soc. 1972, 94, 6190.
11. E. Winterfeldt, Synthesis 1975, 617.
12. A. J. Mancuso, D. Swern, Synthesis 1981, 165.
13. a) E. J. Corey, R. Greenwald, M. Chaykovsky, J. Org. Chem. 1963, 28, 1128;
14. b) J. A. Marshall, M. T. Pike, R. D. Carroll, ibid. 1966, 31, 2933.
15. a) J. A. Marshall, W. F. Huffmann, J. A. Ruth, J. Am. Chem. Soc. 1972, 94, 4691;
16. b) G. Magnusson, Tetrahedron Lett. 1977, 2713.
17. 2, RT): The trans-4:cis-4 ratio is 4:1 after 1 day and 3:2 after 4 days; the diastereomers were separated after Wittig olefination to form 5; yield 65-68%.
18. Usually, allyl chlorides generated by Von-Braun-degradation of the intermediate acylammonium salts were isolated as side products. J. H. Cooley, E. J. Evain, Synthesis 1989, 1. For preparative details see refs. [1] and [2]. Some decrease of the yields had to be taken in account after HPLC separations.
19. 1H-NMR); NOE analysis: H-4β ⇒ H-6 (6); H-6 ⇒ H-4β (5); H-5 ⇒ H-7α (10); H-7α ⇒ H-5 (13). Amide ("E"): H-3 ⇒ H-9α (15); H-9α ⇒ H-3 (28). Relative configuration of C-3 and C-8 (⇒ trans): H-3 ⇒ H-5 (4), H-9α (15); H-5 ⇒ H-3 (3), H-9α (3); H-9α ⇒ H-3 (28), H-5 (5); H-8 ⇒ H-6 (3), H-9β (2); H-9β ⇒ H-8 (3).
20. M. Nagatsuma, F. Shirai, N. Sayo, T. Nakai, Chem. Lett. 1984, 1393.
21. The relative configuration was not determined, because under the conditions of measurement ketenes and acylammonium salts were formed. The protonation and acylation of trans-5 (R = H) with non-ketene-generating acyl units proceeded diastereoselectively syn with respect to the vinyl and anti to the TBSO group, which was proved by NOE experiments.
22. a) D. A. Evans, J. Bartoli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127;
23. b) W. Richter, W. Sucrow, Chem. Ber. 1971, 104, 3679.
24. a) W. S. Johnson, V. J. Bauer, J. L. Margrave, M. A. Frisch, L. H. Dreger, W. N. Hubbard, J. Am. Chem. Soc. 1961, 83, 606;
25. b) P. Vittorelli, H.-J. Hansen, H. Schmid, Helv. Chim. Acta 1975, 58, 1293;
26. c) R. L. Vance, N. G. Rondan, K. N. Houk, F. Jensen, W. T. Borden, A. Komornicki, E. Wimmer, J. Am. Chem. Soc. 1988, 110, 2314.
27. a) G. Büchi, J. E. Powell, J. Am. Chem. Soc. 1970, 92, 3162;
28. b) M. M. Abelmann, R. F. Funk, J. D. Munger, ibid. 1982, 104, 4030.
29. 1/2 bei 133°C: 120 h: A. C. Cope, B. A. Pawson, ibid. 1965, 87, 3649.
30. 1/2 bei 133°C: 120 h: A. C. Cope, B. A. Pawson, ibid. 1965, 87, 3649.
31. Synthesis of azoninones without any stereogenic centers: E. D. Edstrom, J. Am. Chem. Soc. 1991, 113, 6690.
32. 13C HETCOR analysis for 12, 13, and 14: in each case coupling C-1 (Ar) with H-8; C-8 (d, δ ≈ 40) with H-8 ⇒ substituent Se; C-8a (d, δ ap; 60) with H-8a ⇒ substituent N. 12: NOE analysis: Relative configuration of C-2, C-6, C-8 and C-8a (⇒ β: H-2, H-8a; α: H-6, H-8): H-2 ⇒ H-8a (9); H-8a ⇒ H-2 (6), H-7β (8); H-6 ⇒ H-8 (7), H-7a (7); H-8 ⇒ H-6 (7), H-1α (4); H-1α ⇒ H-8 (8). 13: NOE analysis: Relative configuration of C-2, C-6, C-8, and C-8a (⇒ β: H-2, H-8; α: H-6, H-8a): H-1β ⇒ H-2 (9), H-8 (10), H-2 ⇒ H-1β (6), H-3β (5); H-8 ⇒ H-1β (5), H-7β (4); H-6 ⇒ H-7α (4), H-7α ⇒ H-6 (11); H-8a ⇒ H-7α (10), H-1α (5); H-7α ⇒ H-6 (11), H-8a (5); H-1α ⇒ H-8a (5). 14: NOE analysis: (irradiation of H-x ⇒ enhancement at H-y [%]) relative configuration of C-2, C-6, C-8, and C-8a (⇒ β: H-6, H-8a; α: H-2, H-8): H-1β ⇒ H-8a (10); H-5β ⇒ H-7β (3), H-8a (3); H-1β ⇒ H-5β (3), H-8a (2); H-8a ⇒ H-1β (8), H-5β (7), H-7β (7); H-6 ⇒ H-7β (4); H-2 ⇒ H-1α (8), H-1α ⇒ H-2 (4), H-8 (11); H-8 ⇒ H-1α (11), H-7α (8). For IR data see Table 1.
33. a) D. Y. Curtin, Rec. Chem. Prog. 1954, 15, 111;
34. b) J. I. Seeman, Chem. Rev. 1983, 83, 83.
35. 3).