A new asymmetric synthesis of trans-hydroisoquinolones

Organic Letters

Volumn 3, Issue 8, 2001, Pages 1229-1232

  Kamatani, Asayuki ^a,b   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Banyu Pharmaceutical Company   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATION; CYCLOHEXANOL DERIVATIVE; OXYGEN; QUINOLONE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; SYNTHESIS;

CARBON; CATIONS; CYCLOHEXANOLS; MODELS, CHEMICAL; OXYGEN; QUINOLONES;

EID: 0035912359     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015696v     Document Type: Article

References (32)

1. Bentley, K. W. Nat. Prod. Rep. 1999, 16, 367-388 and references therein.
2. Lednicer, D.; Mitscher, L. A. The Organic Chemistry of Drug Synthesis; Wiley: New York, 1997; Vol. 7 and earlier volumes in this series.
3. For brief reviews, see: (a) Overman, L. E. Acc. Chem. Res. 1992, 25, 352-359.
4. (b) Overman, L. E. Aldrichim. Acta 1995, 28, 107-120.
5. (c) Overman, L. E. In Selectivities in Lewis Acid-Promoted Reactions; NATO ASSI Series 289; Schinzer, D., Ed.; Kluwer Academic: Dordrecht, The Netherlands, 1989; pp 1-20.
6. Recent illustrative examples include (a) MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391-10392.
7. (b) Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927-8940.
8. (c) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223-226.
9. (d) Overman, L. E.; Pennington, L. D. Org. Lett. 2000, 2, 2683-2686.
10. (e) Molina-Ponce, A.; Overman, L. E. J. Am. Chem. Soc. 2000, 122, 8672-8676.
11. Cohen, F.; MacMillan, D. W. C.; Overman, L. E.; Romero, A. Org. Lett. 2001, 3, 1225-1228; accompanying paper in this issue.
12. For other Prins-pinacol reactions that involve hydride migrations, see: (a) Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092-1093.
13. (b) Overman, L. E.; Pennington, L. D. Can. J. Chem. 2000, 78, 732-738.
14. 8
15. (a) Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Chem. Commun. 1983, 469-470.
16. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. J. Am. Chem. Soc. 1987, 109, 5551-5553.
17. (c) For a review, see: Itsuno, S. Org. React. 1998, 52, 395-576.
18. Kamatani, A.; Overman, L. E. J. Org. Chem. 1999, 64, 8743-8744.
19. For a review of the Suzuki reaction, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
20. For recent reviews of N-acyliminium ion chemistry, see: (a) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, Chapter 4.5.
21. (b) de Koning, H.; Speckamp, W. N. In Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995, Vol. E21b, Chapter D.1.4.5.
22. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
23. 5 However, destabilizing nonbonded interactions between the developing axial Cl substituent and the bulky siloxy would be severe in such a cyclization transition state.
24. Enantiomeric purity was determined (a) by capillary GLC analysis using a J&W CyclodexB column or (b) by HPLC analysis using a Daicel OD-H column. In all cases, the analysis was calibrated with a sample of the racemate.
25. 6 at elevated temperature.
26. 4, followed by Swern oxidation of the resulting amino alcohol product.
27. 4; details are provided in Supporting Information.
28. (a) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
29. (b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
30. Chamberlin, A. R.; Chung, J. Y. L. J. Am. Chem. Soc. 1983, 105, 3653-3656.
31. Hiemstra, H.; Fortgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 1985, 26, 3155-3158.
32. 6) exhibited a diagnostic triplet of doublets (J = 11.8, 3.8 Hz) for H-4a at δ 2.47 ppm, and the NOESY spectrum showed a strong correlation between H-1 and H-8a. Similar experiments established the structure of the other 1-substituted 5-oxooctahydroisoquinolines reported in Table 1.