Diastereoselective Introduction of Carbon Chain to Pyrrolidone Derivatives

Synlett

Volumn 1996, Issue 8, 1996, Pages 751-752

  Sato, Kentaro ^a   Koga, Tsukasa ^a   Masuya, Keiichi ^a   Tanino, Keiji ^a   Kuwajima, Isao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002936358     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5538     Document Type: Article

References (19)

1. (a) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 355-396.
2. (b) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 893-1109.
3. Tohyama, Y.; Tanino, K.; Kuwajima, I. J. Org. Chem. 1994, 59, 518.
4. (a) Tanino, K.; Nakamura, T.; Kuwajima, I. Tetrahedron Lett. 1990, 31, 2165.
5. (b) Tanino, K.; Shoda, H.; Nakamura, T.; Kuwajima, I. ibid. 1992, 33, 1337.
6. (c) Nakamura, T.; Tanino, K.; Kuwajima, I. Chem. Lett. 1992, 1425.
7. (d) Nakamura, T.; Tanino, K.; Kuwajima, I. Tetrahedron Lett., 1993, 34, 477.
8. (e) Masuya, K.; Tanino, K.; Kuwajima, I. ibid. 1994, 35, 7965.
9. (a) Torssell, K. B. G. Natural Product Chemistry; John Wiley & Sons: New York, 1983; Chapter 7.
10. (b) Pinder, A. R. Nat. Prod. Reports, 1992, 9, 491.
11. (c) Plunkett, A. O. Nat. Prod. Reports, 1994, 11, 581.
12. IIa and IIc were easily prepared from corresponding α-hydroxy lactam: Takacs, J. M.; Weidner, J. J. J. Org. Chem. 1994, 59, 6480. See also ref. 7b.
13. 3) δ 1.0-1.2 (m, 24 H), 1.8-2.5 (m, involving a singlet at 2.16, 7 H), 3.30-3.40 (m, 1 H), 3.65-3.75 (m, 1 H), 4.07 ( d, J = 7.2 Hz, 1 H), 4.97 (d, J = 7.2 Hz, 1 H), 6.80 (s, 1 H), 7.2-7.4 (m, 5 H).
14. (a) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. These lactams are precursors of pyrrolizidine alkaloids heliotridane and pseudoheliotridane. For an example of synthesis of (-)-heliotridane, see: Doyle, M. P.; Kalinin, A. V. Tetrahedron Lett. 1996, 37, 1371.
15. (a) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868. These lactams are precursors of pyrrolizidine alkaloids heliotridane and pseudoheliotridane. For an example of synthesis of (-)-heliotridane, see: Doyle, M. P.; Kalinin, A. V. Tetrahedron Lett. 1996, 37, 1371.
16. (b) Diastereofacialselective addition reactions to pyrrolidine derivatives bearing chiral auxiliaries: Polniaszek, R. P.; Belmont, S. E.; Alvarez, R. J. Org. Chem. 1990, 55, 215. See also: Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 6119.
17. (b) Diastereofacialselective addition reactions to pyrrolidine derivatives bearing chiral auxiliaries: Polniaszek, R. P.; Belmont, S. E.; Alvarez, R. J. Org. Chem. 1990, 55, 215. See also: Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 6119.
18. IId was derived from (R)-1-amino-1-phenyl-2-methoxyethane: Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem. 1978, 43, 892.
19. Diastereofacial selective addition reactions of organomethallics to acyclic imine derived from (R)-1-amino-1-phenyl-2-methoxyethane: Ukaji, Y.; Watai, T.; Sumi, T.; Fujisawa, T. Chem. Lett. 1991, 1555.