Tert-Butylsulfonyl (Bus), a New Protecting Group for Amines

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8604-8606

  Sun, Pu ^a   Weinreb, Steven M ^a   Shang, Maoyu ^b  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000822788     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971455i     Document Type: Article

References (18)

1. For reviews, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York; 2nd ed.; 1991; pp 379-86. Barton, J. W. Protection of N-H Bonds and NRa. In Protective Groups in Organic Chemistry; McOmie, J. F. W., Ed.; Plenum: New York, 1973; pp 73-74.
2. For reviews, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York; 2nd ed.; 1991; pp 379-86. Barton, J. W. Protection of N-H Bonds and NRa. In Protective Groups in Organic Chemistry; McOmie, J. F. W., Ed.; Plenum: New York, 1973; pp 73-74.
3. Vedejs, E.; Lin, S.; Klapars, A.; Wang, J. J. Am. Chem. Soc 1996, 118, 9796 and references therein.
4. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373. Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831. See also: Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253.
5. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373. Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831. See also: Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253.
6. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373. Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831. See also: Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253.
7. Weinreb, S. M.; Demko, D. M.; Lessen, T. A.; Demers, J. P. Tetrahedron Lett. 1986, 27, 2099.
8. King, J. F.; Lam, J. Y. L.; Dave, V. J. Org. Chem. 1995, 60, 2831 and references therein.
9. Richey, H. G., Jr.; Farkas, J., Jr. J. Org. Chem. 1987, 52, 479.
10. Acidic workup of these sulfinamides should be avoided since partial hydrolysis occurs, lowering the yield of product. See: Wagner, B. J.; Doi, J. T.; Musker, W. K. J. Org. Chem. 1990, 55, 5940.
11. Dimethyldioxirane also effects oxidation of sulfinamides 2 to sulfonamides 3.
12. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
13. Not surprisingly, considering the work of Richey and Farkas, 6 N-Bus-pyrrol idine is unreactive toward sec-BuLi/TMEDA. We thank A. Greenberg for conducting this experiment.
14. Kricheldorf, H. R. Angew. Chem., Int. Ed. Engl. 1978, 17, 442.
15. The authors have deposited X-ray data with the Cambridge Cristallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
16. 2 by the solution.
17. In this case, 1.5 equiv of tert-butylsulfinyl chloride was used to minimize formation of the N,N-bis(tert-butylsulfinyl)amine.
18. The amount of ruthenium catalyst used is crucial. The color of the upper aqueous layer should be brown, not black. Low yields of sulfonamide were normally obtained if too much catalyst was used.