Facial selectivity of the sharpless bromine catalyzed aziridination

Heterocycles

Volumn 62, Issue , 2004, Pages 635-642

  Schmitt, Aaron C ^a   Smith, Catherine M ^a   Voight, Eric A ^a   O'Doherty, George A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4,4 DIBROMO 8 (TOLUENE 4 SULFONYL) 8 AZATRICYCLO[5.1.0.0]OCTANE; 7,7 DIBROMO 3 NORCARENE; ALKENE; BROMINE; EPOXIDE; OCTANE; UNCLASSIFIED DRUG;

ARTICLE; AZIRIDINATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CIS ISOMER; DIASTEREOISOMER; STEREOCHEMISTRY; STEREOSPECIFICITY; TRANS ISOMER;

EID: 0346459967     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-s(p)57     Document Type: Article

References (15)

1. This paper is dedicated to Professor Leo A. Paquette on the occasion of his 70th birthday.
2. University of Minnesota Undergraduate Research Opportunity Program (UROP) Participant
3. For a review of dihalocyclopropane ring opening reactions, see: (a) M. G. Banwell and M. E. Reum, in 'Advances In Strain In Organic Chemistry,' Vol. 1, ed. by B. Halton, Jai Press, Inc. Greenwich, CT, 1991.
4. For Lewis acid catalyzed opening of aziridines see: B. A. B. Prasad, G. Sekar, and V. K. Singh, Tetrahedron Lett., 2000, 41, 4677 and references therein.
5. J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, and K. B. Sharpless, J. Am. Chem. Soc., 1998, 120, 6844.
6. Upon completion of this work, similar stereoselectivity for this reaction were discovered in a cyclopentenol substrate, by O'Brien, see: D. Caine, P. O'Brien, and C. M. Rosser, Org. Lett., 2002, 4, 1923.
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9. We have found that freshly prepared tetrabutylammonium perbromide provided similarly good yields of 4 and 7.
10. Due to the high degree of H-H J-coupling and the twist boat nature of 4 all nOe experiments were inconclusive in determining the relative stereochemistry between the cyclopropane and aziridine rings.
11. (a) J. Rudolph, K. L. Reddy, J. P. Chiang, and K. B. Sharpless, J. Am. Chem. Soc., 1997, 119, 6189.
12. (b) H. Adolfsson, A. Converso, and K. B. Sharpless, Tetrahedron Lett., 1999, 40, 3991.
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