Synthesis of 10,11-didehydro- and 10,11-dihydro-quincorine and of the quincoridine analogs: Functionalized and enantiopure 1-azabicyclo[2.2.2]- octanes with four stereogenic centers

Tetrahedron Asymmetry

Volumn 9, Issue 20, 1998, Pages 3717-3722

  Schrake, Olaf ^a   Braje, Wilfried ^a   Hoffmann, H M R ^a   Wartchow, R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 0032561407     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00364-4     Document Type: Article

References (9)

1. Hoffmann, H. M. R.; Plessner, T.; von Riesen, C. Synlett 1996, 690. QCI and QCD are available from Buchler GmbH, Harxbütteler Str. 3, D-38110 Braunschweig, fax: +(0)5307-931-31.
2. Hoffmann, H. M. R.; Schrake, O. Tetrahedron: Asymmetry 1998, 9, 1051.
3. Dehmlow, E. V.; Lissel, M. Tetrahedron 1981, 37, 1653.
4. QCI solidifies on prolonged cooling below 0°C and melts at room temperature (23-26°C). C. von Riesen, personal communication.
5. f-values for QCI/QCD: 0.24; 10,11-dihydro-QCI/QCD: 0.18; 10,11-didehydro-QCI/QCD: 0.16.
6. Wynberg, H.; Smaardijk, A J. Org. Chem. 1987, 52, 135.
7. (a) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069.
8. (b) Norrby, P.; Kolb, H. C.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 8470.
9. The angles given in the left hand column correspond to those on the right, but are numbered according to different conventions (IUPAC for 1-azabicyclo[2.2.2]octanes and traditional nomenclature for cinchona alkaloids). Detailed X-ray diffraction data will be submitted to Z. Krist-NCS.