Reaction of monocarbonyl iodonium ylides with activated imines: Stereoselective synthesis of trans- and cis-α,β-aziridino ketones

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5569-5570

  Ochiai, Masahito ^a   Kitagawa, Yutaka ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; KETONE DERIVATIVE; ORGANOIODINE DERIVATIVE;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032581665     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01122-8     Document Type: Article

References (10)

1. 1. For reviews of iodonium ylides, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 18.
2. (b) Varvoglis, A. Synthesis 1984, 709.
3. (c) Moriarty, R. M.; Void, R. K. Synthesis 1990, 431.
4. (d) Varvoglis, A. The Chemistry of Poly coordinated Iodine; VHC Publishers: New York, 1992; Chapter 6.
5. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
6. 2. Ochiai, M.; Kitagawa, Y.; Yamamoto, S. J. Am. Chem. Soc. 1997, 119, 11598.
7. 4p-Me) expect the reactivity order toward nucleophiles, PhCH=NTs 2i > PhCHO> PhCH=NPh. See: Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Chen, M.-B. J. Org. Chem. 1996, 61, 4641.
8. 4. (a) Pines, S. H.; Kozlowski, M. A.; Karady, S. J. Org. Chem. 1969, 34, 1621.
9. (b) Heine, H. W.; Kaplan, M. S. J. Org. Chem. 1967, 32, 3069.
10. 5. For the stereoselective synthesis of α,β-aziridino ketones using monocarbonyl bismuthonium ylides, see: Matano, Y.; Yoshimune, M.; Suzuki, H. J. Org. Chem. 1995, 60, 4663.