Transformations of resin-bound pyridinium ylides: I. A stereoselective synthesis of 2,2,3-trisubstituted cyclopropanecarboxylates

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 7951-7954

  Vo, Nha Huu ^a   Eyermann, Charles Joseph ^a   Hodge, C Nicholas ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; PYRIDINIUM DERIVATIVE;

ARTICLE; CONFORMATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030727607     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10081-8     Document Type: Article

References (11)

1. Vo, N.H.; Eyermann, C.J.; Hodge, C.N. 213th ACS National Meeting, San Francisco, April 13-17 1997, MEDI-308: American Chemical Society, Washington, D.C.
2. a. Burgess, K.; Ho, K.; Pal, B. J. Am. Chem. Soc. 1995, 117, 3808-3819
3. b. Rao, S.; Ramnayaran, K.; Balaji, V.N. Peptides 1994, 181-196. Basava, C.; Anantharamaiah, G.N., Eds.; Birkheuser, Boston.
4. More than fifty mono- and poly-substituted cyclopropanes in numerous therapeutic classes are listed in the Comprehensive Medicinal Chemistry Database (CMC-3D 94.1, available from MDL Information Systems, San Leandro, CA; compiled from Comprehensive Medicinal Chemistry, 1990, Vol. 6; Eds. Hansch, C.; Sammes, P.G.; Taylor, J.B.; Drayton, C.J.; Pergamon, Oxford, UK. See also Koskinen, A.M.P.; Hassila, H. Acta Chem. Scand. 1996, 50, 323-327.
5. More than fifty mono- and poly-substituted cyclopropanes in numerous therapeutic classes are listed in the Comprehensive Medicinal Chemistry Database (CMC-3D 94.1, available from MDL Information Systems, San Leandro, CA; compiled from Comprehensive Medicinal Chemistry, 1990, Vol. 6; Eds. Hansch, C.; Sammes, P.G.; Taylor, J.B.; Drayton, C.J.; Pergamon, Oxford, UK. See also Koskinen, A.M.P.; Hassila, H. Acta Chem. Scand. 1996, 50, 323-327.
6. Reaction of sulfonium-(2-oxo)ethylide with ethylidene malononitrile: Wilkerson, M.G., Norton, S.J., J. Agric. Food Chem. 1981, 29, 572-576; Payne, G.B. U.S. Patent 3,397,223.
7. Reaction of malonate or malononitrile with 3-bromo-5-methoxyfuran-2(5H)-one, Farina, F.; Maestro, M.C.; Martin, M.V.; Soria, M.L. Tetrahedron 1987, 43, 4007-4114.
8. a. Shestopalov, A.M.; Sharanin, Y.A.; Litvinov, V.P.; Nefedov, O.M. Zh. Org. Khim. 1989, 25, 1111-1112;
9. b. ibid., Ser. Khim. 1991, 146-155.
10. Texier-Boullet, F.; Foucaud, A. Tetrahedron Lett. 1982, 23, 4927-4928.
11. 6: C, 56.25; H, 6.29. Found: C, 56.38; H, 6.20.