Unexpected diastereoselectivity in AD of an L-proline-derived 1,1- disubstituted alkene

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 1029-1032

  Gardiner, John M ^a   Bruce, Sarah E ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; PROLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032567964     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10695-5     Document Type: Article

References (18)

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4. 2. Asymmetric 'L-shaped' model involving a heterocyclic 'active site' floor and a quinoline 'wall' available for face-to-edge stabilization: (a) Norrby, P.-O.; Kolb, H. C.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 8470.
5. (b) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35.
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7. 3. Symmetric 'binding cleft' model (involving both quinoline moiteies in face-to-face π-interactions): (a) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1995, 117, 10805.
8. (b) Corey, E. J.; Noe, M. C.; Guzman-Perez, A. J. Am. Chem. Soc. 1995, 117, 10817.
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12. 6. Iwashima, M.; Kinsho, T.; Smith, A. B., III Tetrahedron Lett. 1995, 36, 2199.
13. 7. Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825.
14. 8. Overman, L. E.; Bell, K. L. J. Am. Chem. Soc. 1981, 103, 1851. Stereostructures of epoxides were in this case established through conversion to stereochemcially unambiguous known targets.
15. 9. Perkin Elmer 8500 gas chromatograph. SE30 dimethyl silicone capillary column 12m × 0.25mm. Conditions: ramped over 80-280 °C at 10 °C per min.
16. 10. Spectra were recorded at 300 MHz on a Bruker AC-300.
17. 8 and comparison of the NMR spectra of the AD-derived epoxides with the NMR data reported allows a clear assignment of epoxide structure and a retrospective assignment of diol configurations.
18. 12. All new compounds provided satisfactory analytical data.