Cyclic-fused azomethine-, imidate-, and thioimidate methylides: An efficient regiocontrolled entry into spiro-fused pyrrolidines

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5163-5166

  Fishwick, Colin W G ^a   Foster, Richard J ^a   Carr, Robin E ^b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPYRAN DERIVATIVE; BENZOTHIOPHENE; INDAN DERIVATIVE; PYRROLIDINE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; METHYLATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0030586101     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01026-X     Document Type: Article

References (18)

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3. 2. See: Ireland, R.E.; Habich, D. Tetrahedron Lett., 1980, 21, 1389.
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5. 4. For some related cycloadditions of imidate, amidine and thioimidate ylides, see: a) Livinghouse, T.; Smith, R. J. Chem. Soc. Chem. Comm,. 1983, 210.
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12. 5. See: Berube, A.; Lessard, A. Can. J. Chem., 1982, 1127.
13. 6. See: Griller, D.; McPhee, D.J.; Letellier, M. Synth. Commun.,1988, 18, 1975.
14. 3) 2.09(3H,s,NMe), 2.70(1H,m,Hα-7), 3.00(3H,s,NMe), 3.50(2H,m,Hβ-7,Hα-8), 3.71(1H,d,J=7Hz,Hα-9), 4.11((2H,AB quartet,J=12Hz,H-2), 7.20-7.31(4H,m,ArH).
15. 8. Stereoisomerism in the related [4.4] spiroketals is known, see: Kitching, W.; Lawson, E.N.; Woodhall, J.F.; Nishiyami, T. J. Org. Chem., 1989, 54, 2183.
16. 9. For some similiar examples, see: a) Fishwick, C.W.G.; Foster, R.J.; Carr, R.E. Tetrahedron Lett., 1995, 36, 9409.
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