Cycloaddition of homochiral imidazolinium ylides: A route to optically active pyrroloimidazoles

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1707-1710

  Jones, Raymond C F ^a,b   Howard, Kevin J ^a   Snaith, John S ^a,b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b OPEN UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; PYRROLO[1,2 A]IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029969515     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00113-X     Document Type: Article

References (14)

1. Jones, R.C.F.; Nichols, J.R.; Cox, M.T. Tetrahedron Lett., 1990, 31, 2333.
2. For other examples of conformationally restrained azomethine ylides see: Harwood, L.M.; Lilley, I.A. Tetrahedron Lett., 1993, 34, 537; Williams, R.M.; Zhai, W.; Aldous, D.J.; Aldous, S.C. J. Org. Chem., 1992, 57, 6527. For a related example of an azomethine ylide with rotational freedom see: Rouden, J.; Royer, J.; Husson, H.-P. Tetrahedron Lett., 1989, 30, 5133.
3. For other examples of conformationally restrained azomethine ylides see: Harwood, L.M.; Lilley, I.A. Tetrahedron Lett., 1993, 34, 537; Williams, R.M.; Zhai, W.; Aldous, D.J.; Aldous, S.C. J. Org. Chem., 1992, 57, 6527. For a related example of an azomethine ylide with rotational freedom see: Rouden, J.; Royer, J.; Husson, H.-P. Tetrahedron Lett., 1989, 30, 5133.
4. For other examples of conformationally restrained azomethine ylides see: Harwood, L.M.; Lilley, I.A. Tetrahedron Lett., 1993, 34, 537; Williams, R.M.; Zhai, W.; Aldous, D.J.; Aldous, S.C. J. Org. Chem., 1992, 57, 6527. For a related example of an azomethine ylide with rotational freedom see: Rouden, J.; Royer, J.; Husson, H.-P. Tetrahedron Lett., 1989, 30, 5133.
5. Jones, R.C.F.; Howard, K.J.; Snaith, J.S. following Letter.
6. Jones, R.C.F.; Turner, I.; Howard, K.J. Tetrahedron Lett., 1993, 34, 6329.
7. Jones, R.C.F.; Howard, K.J. J. Chem. Soc., Perkin Trans. 1, 1993, 2391.
8. All new compounds gave spectral data (IR, NMR, MS) in accord with the assigned structure, and satisfactory combustion analysis or accurate mass measurement.
9. +, 4%), 309 (29), 308 (100), 249 (36), 217 (13), 130 (12), 104 (34), 91 (87).
10. For example, for 5a, n.O.e. enhancements were observed between the protons on the following carbons: C5→C3, C6(pro-S)→C5, C7(Me)→C6(pro-R), C7(Me)->C7a
11. -1; cf. Jones, R.C.F.; Howard, K.J. Electronic Conference on Trends in Organic Chemistry (ECTOC-1) ISBN 0 85404 899 5, Eds. Rzepa, H.S.; Goodman, J.M. (CD-ROM), Royal Society of Chemistry publications, 1995. see also http://www.ch.ic.ac.uk/ectoc/
12. -1; cf. Jones, R.C.F.; Howard, K.J. Electronic Conference on Trends in Organic Chemistry (ECTOC-1) ISBN 0 85404 899 5, Eds. Rzepa, H.S.; Goodman, J.M. (CD-ROM), Royal Society of Chemistry publications, 1995. see also http://www.ch.ic.ac.uk/ectoc/
13. Jones, R.C.F.; Howard, K.J.; Snaith, J.S.; Steel, P.J. manuscript in preparation.
14. There is no evidence for the ring opening equilibrium observed in the achiral series, ref. 2.