Ring-opening reactions of 3-aryl-1-benzylaziridine-2-carboxylates and application to the asymmetric synthesis of an amphetamine-type compound

Helvetica Chimica Acta

Volumn 90, Issue 1, 2007, Pages 128-142

  Manaka, Tomoyuki ^a   Nagayama, Shin Ichiro ^a   Desadee, Wannaporn ^a   Yajima, Naoki ^a   Kumamoto, Takuya ^a   Watanabe, Toshiko ^a   Ishikawa, Tsutomu ^a   Kawahata, Masatoshi ^b   Yamaguchi, Kentaro ^b  

^a CHIBA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHETAMINE; AROMATIC MOIETY; AZIRIDINES; RING-OPENING REACTIONS;

AMINO ACIDS; CATALYSIS; DERIVATIVES; HYDROGENATION; RING OPENING POLYMERIZATION; STEREOCHEMISTRY;

CARBOHYDRATES;

1 BENZYLAZIRIDINE 2 CARBOXYLATE DERIVATIVE; AMPHETAMINE; AROMATIC COMPOUND; AZIRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; DIASTEREOISOMER; PRIORITY JOURNAL; RING OPENING; STEREOSPECIFICITY;

EID: 33846595303     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200790006     Document Type: Article

References (17)

1. A. K. Yudin, in 'Aziridines and Epoxides in Organic Synthesis', Wiley-VCH, New York, 2005.
2. G. Cardillo, L. Gentilucci, A. Tolomelli, Aldrichim. Acta 2003, 36, 39.
3. W. K. Lee, H.-J. Ha, Aldrichim. Acta 2003, 36, 57.
4. W. McCoull, F. A.Davis, Synthesis 2000, 1347.
5. X. E. Hu, Tetrahedron 2004, 60, 2701.
6. J. Legters, L. Thijs, B. Zwanenburg, Recl. Trav. Chim. Pays-Bas 1992, 111, 16.
7. C. Xiong, W. Wang, C. Cai, V. J. Hruby, J. Org. Chem. 2002, 67, 1399.
8. C. Loncaric, W. D. Wulff, Org. Lett. 2001, 3, 3675.
9. G. Cardillo, L. Gentilucci, A. Tolomelli, Tetrahedron Lett. 1999, 40, 8261.
10. K. Hada, T. Watanabe, T. Isobe, T. Ishikawa, J. Am. Chem. Soc. 2001, 123, 7705.
11. W. Disadee, T. Ishikawa, J. Org. Chem. 2005, 70, 9399.
12. T. Haga, T. Ishikawa, Tetrahedron 2005, 61, 2857.
13. S. Futagawa, T. Inui, T. Shiba, Bull. Chem. Soc. Jpn 1973, 46, 3308.
14. F. A. Carey, R. J. Sundberg, in 'Advanced Organic Chemistry', 4th edn., Part A, Kluwer Academic/ Plenum Publishers, New York, 2000, p. 112.
15. G. A. Molander, P. J. Stengel, J. Org. Chem. 1995, 60, 6660.
16. T. Nishikawa, S. Kajii, K. Wada, M. Ishikawa, M. Isobe, Synthesis 2002, 1658.
17. D. A. Quagliato, P. M. Andrae, E. M. Matelan, J. Org. Chem. 2000, 65, 5037.