Unusual C-C cleavage during reduction of a β-aminonitroalkene

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4493-4496

  Freeman, Jeremiah P ^a   Laurian, Lloyd ^b   Szmuszkovicz, Jacob ^a,b  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033546103     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00818-7     Document Type: Article

References (8)

1. 1. The work described here was performed at the Upjohn Company (J.S. is now at the University of Notre Dame.)
2. 2. Freeman, J.P.; Michalson, E.T.; D'Andrea, S.V.; Baczynskyj, L.; VonVoightlander, P.F.; Lahti, R.A.; Smith, M.W.; Lawson, C.F.; Scahill, T.A.; Miszak, S.A.; Szmuszkovicz, J. J. Med. Chem. 1991, 34, 1891. D'Andrea, S.V.; Freeman, J.P.; VonVoightlander, P.F.; Szmuszkovicz, J. Tetrahedron, 1991, 47, 6157.
3. 2. Freeman, J.P.; Michalson, E.T.; D'Andrea, S.V.; Baczynskyj, L.; VonVoightlander, P.F.; Lahti, R.A.; Smith, M.W.; Lawson, C.F.; Scahill, T.A.; Miszak, S.A.; Szmuszkovicz, J. J. Med. Chem. 1991, 34, 1891. D'Andrea, S.V.; Freeman, J.P.; VonVoightlander, P.F.; Szmuszkovicz, J. Tetrahedron, 1991, 47, 6157.
4. 3. Rajappa, S. Tetrahedron, 1981, 37, 1453.
5. 4. Griswold, A.A.; Starcher, P.S. J. Org. Chem. 1966, 31, 357.
6. 5. Swift, G.; Swern, D. J. Org. Chem. 1967, 72, 511.
7. 2O: C, 70.87; H, 9.15; N, 12.72. Found: C, 70.97; H, 9.24; N, 12.93. In a separate experiment a polymorph of compound 6 was isolated by virtue of its insolubility in ether. It melted at 106-110° and was identical by UV, IR and NMR to the compound described above.
8. 2: C, 68.27; H, 7.37; N, 11.37. Found: C, 68.54; H, 7.39; N, 11.23.