The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate

Tetrahedron Asymmetry

Volumn 10, Issue 14, 1999, Pages 2655-2663

  Anderson, Shelby R ^a,b   Ayers, Joshua T ^a   DeVries, Keith M ^b   Ito, Fumitaka ^b   Mendenhall, Debra ^a,b   Vanderplas, Brian C ^b  

^a TRINITY COLLEGE   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZIRIDINE; ETHYLENE OXIDE DERIVATIVE; STYRENE OXIDE;

ALKYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; ISOLATION PROCEDURE; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033575376     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00243-8     Document Type: Article

References (10)

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2. Hanson, R. M. Chem. Rev. 1991, 91, 437.
3. Richardson, P. F.; Nelson, L. T.; Sharpless, K. B. Tetrahedron Lett. 1995, 36, 9241.
4. Dieter, R. K.; Lagu, B.; Dieter, J. W.; Deo, N.; Pennington, W. T. Synlett 1990, 109.
5. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965.
6. Rossiter, B. E.; Miao, G. J. Org. Chem. 1995, 60, 8424.
7. O'Brien, P.; Poumellec, P. Tetrahedron Lett. 1996, 37, 5619.
8. For an earlier discussion of this regioisomer issue, see Atkins, R. K.; Frazier, J.; Moore, L. L.; Weigel, L. O. Tetrahedron Lett. 1986, 27, 2451.
9. A β-amino chloride in a non-benzylic system has been described by Gmeimer and co-workers. See: Gmeimer, P.; Junge, D.; Kartner, A. J. Org. Chem. 1994, 59, 6766.
10. For a recent review on the intermediacy of aziridinium type ions, see: Rayner, C. M. Synlett 1997, 11.