Asymmetric [4+3] cycloadditions from chiral α-chloro imines

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3353-3356

  Kende, Andrew S ^a   Huang, He ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030970291     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00649-7     Document Type: Article

References (19)

1. Reviews of [4+3] cycloadditions include (a) Mann, J. Tetrahedron 1986, 42, 4611;
2. ( b) Rigby, J. H.; Pigge, F. C. Org. Reactions (N.Y.), 1997, in press.
3. (a) Lautens, M.; Aspiotis, R.; Colucci, J. J. Am. Chem. Soc. 1996, 118, 10930;
4. (b) Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774.
5. De Kimpe, N.; Palamareva, M.; Verne, R.; De Buyck, L.; Schamp, N. J. Chem. Res. (S) 1986, 190. For an example of a 1-phthaloylamino-substituted oxyallyl species in a [4+3] cycloaddition, see Walters, M. A.; Arcand, H. R.; Lawrie, D. J. Tetrahedron Lett. 1995, 36, 23.
6. De Kimpe, N.; Palamareva, M.; Verne, R.; De Buyck, L.; Schamp, N. J. Chem. Res. (S) 1986, 190. For an example of a 1-phthaloylamino-substituted oxyallyl species in a [4+3] cycloaddition, see Walters, M. A.; Arcand, H. R.; Lawrie, D. J. Tetrahedron Lett. 1995, 36, 23.
7. 13C NMR data.
8. 4, filtered, and concentrated. The residue was separated by silica gel chromatography (EtOAc-hexanes, 1:5) to give 4a (168 mg, 1.11 mmol, 37%).
9. 3) (60% ee). Fohlisch, B.; Sendelbach, S.; Bauer, H. Liebigs Ann. Chem. 1987, 1.
10. Turro, N. J.; Edelson, S. S.; Williams, J. R.; Darling, T. R.; Hammond, W. B. J. Am. Chem. Soc. 1969, 91, 2283.
11. 3: 285.1370, found: 285.1365.
12. 3) (25% ee). Hoffmann, H. M. R.; Eggert, U.; Gibbels, U.; Giesel, K.; Koch, O.; Lies, R.; Rabe, J. Tetrahedron 1988, 44, 3899.
13. 3 and the corresponding ee was determined.
14. 2: 156.1148, found: 156.1150.
15. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512;
16. (b) Ohtani, I.; Kusumi, T.; Kashman, H. J. Am. Chem. Soc. 1991, 113, 4092;
17. 1H NMR signals of the gem dimethyls of the major (3S, 2′R)-MTPA ester appear at δ 0.82 (axial) and 1.03 (equatorial), both upfield to those of the minor (3R, 2′R)-MTPA ester at δ 0.92 (axial) and 1.07 (equatorial).
18. 1 with a = 6.186(1), b = 14.001(3), c = 20.487(3) Å, Z = 4 and R = 2.9%; coordinates have been deposited with the Cambridge Crystallographic Data Center.
19. Lucero, M. J.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 826 and references cited therein.