A practical and scalable synthesis of N-halo compounds: 2-chloro-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Organic Syntheses

Volumn 87, Issue , 2010, Pages 8-15

  Zhong, Yong Li ^a   Bulger, Paul G ^b   Newman, Stephen G ^b   Lautens, Mark ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952562901     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.1002/0471264229.os087.02     Document Type: Article

References (20)

1. Liu, J. F.; Heathcock, C. H. J. Org. Chem. 1999, 64, 8263-8266.
2. Stocking, E. M.; Sanz-Cervera, J. F.; Unkefer, C. J.; Williams, R. M. Tetrahedron 2001, 57, 5303-5320.
3. Maughan, M. A. T.; Davies, I. G.; Claridge, T. D. W.; Courtney, S.; Hay, P.; Davis, B. G. Angew. Chem. Int. Ed. 2003, 42, 3788-3792.
4. For further selected examples, see: (a) Zhong, Y.-L., Krska, S. W.; Zhou, H.; Reamer, R. A.; Lee, J.; Sun, Y.; Askin, D. Org. Lett. 2009, 11, 369-372.
5. (b) Drouin, A.; Lessard, J. Tetrahedron Lett. 2006, 47, 4285-4288.
6. (c) Cossy, J.; Tresnard, L.; Pardo, D. G. Tetrahedron Lett. 1999, 40, 1125-1128.
7. (d) Stella, L. Angew. Chem. Int. Ed. Engl. 1983, 22, 337-350.
8. (e) Kovacic, P.; Lowery, M. K.; Field, K. W. Chem. Rev. 1970, 70, 639-655.
9. (a) Smith, J. R. L.; McKeer, L. C.; Taylor, J. M. Org. Synth. Coll. Vol. 8 1993, 167-173.
10. (c) Gassman, P. G.; Dygos, D. K.; Trent, J. E. J. Am. Chem. Soc. 1970, 92, 2084-2090.
11. (a) Zhao, M. M.; McNamara, J. M.; Ho, G.-J.; Emerson, K. M.; Song, Z. J.; Tschaen, D. M.; Brands, K. M. J.; Dolling, U. H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 2002, 67, 6743-6747.
12. (b) Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630-5633.
13. (c) Guillemin, J. C.; Denis, J. M. Synthesis 1985, 1131-1133.
14. (a) Durham, T. B.; Miller, M. J. J. Org. Chem. 2003, 68, 27-34.
15. (b) Herranz, E.; Sharpless, K. B. Org. Synth. Coll. Vol. 7 1990, 223-226.
16. (c) Gassman, P. G.; Campbell, G. A.; Frederick. R. C. J. Am. Chem. Soc. 1972, 94, 3884-3891.
17. Fieser, M. In Reagents for Organic Synthesis, John Wiley and Sons, New York, 1982, Vol. 10, p 67.
18. (a) Mintz, M. J.; Walling, C. Org. Synth. Coll. Vol. 5, 1973, 184-187.
19. Paquette, L. A. In Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons, New York, 1995, Vol. 2, p 890.
20. Zhong, Y.-L.; Zhou, H.; Gauthier, D. R., Jr.; Lee, J.; Askin, D.; Dolling, U. H.; Volante, R. P. Tetrahedron Lett, 2005, 46, 1099-1101.