Crystal structure of (1S,2R,4S,5S)-5-ethynyl-2-hydroxymethyl-1-azabicyclo[2.2.2]octane,(HC 2)(HOCH2)(C7H11N)

Zeitschrift fur Kristallographie - New Crystal Structures

Volumn 216, Issue 2, 2001, Pages 235-236

  Wartchow, R ^a   Frackenpohl, J ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

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EID: 23044527064     PISSN: 14337266     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (13)

1. Quincorine®, pseudoenantiomeric Quincoridine® and the new 10,11-didehydro derivatives 1 nad 2 are available from Buchler GmbH, Harxbütteler Str. 3, D-38110 Braunschweig, Germany.
2. 2. Acta Crystallogr. C39 (1983) 310-312.
3. Hoffmann, H. M. R.; Plessner, T.; von Riesen, C.: The Invention of Chemical Transformations. Functionalized and Enantiopure Quinuclidines from Cinchona Alkaloids. Synlett (1996) 690-692.
4. Hoffmann, H. M. R.; Schrake, O.: Acylation and O-Sulfonylation of Quincorine® and Quincoridine®. Efficient Intramolecular Catalysis. Tetrahedron: Asymmetry 9 (1998) 1051-1057.
5. Pniewska, B.; Suszko-Purzycka, A.: Structure of Quinine Monohydrate Toluene Solvate Acta Crystallogr. C45 (1989) 638-642.
6. Schrake, O.; Braje, W.; Hoffmann, H. M. R.; Wartchow, R.: 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 Centres. Tetrahedron: Asymmetry 9 (1998) 3717-3722.
7. Schrake, O.; Rahn, V. S.; Frackenpohl, J.; Braje, W. M.; Hoffmann, H. M. R.: Novel Bridged Bicyclic α-Amino Acid Esters and Key Derivatives from Quincorine® and Quincoridine®. Org. Lett, 1 (1999) 1607-1610.
8. See also Frackenpohl, J.; Braje, W. M.; Hoffmann, H. M. R.: Cross-coupling reactions in Cinchona alkaloid chemistry: aryl-substituted and dimeric quinine, quinidine, as well as quincorine and quincoridine derivatives. J. Chem. Soc. Perkin Trans, 1 (2001) 47-65.
9. Wartchow, R.; Schrake, O.; Braje, W. M.; Hoffmann, H. M. R.: Crystal structure of (1S,2S,4S,5R)-2-hydroxymethyl-5-ethynyl-1-azabicyclo-[2.2.2]octane. Z. Kristallogr. NCS 214 (1999) 285-286. Correction : The Stereo assignment 5R in this paper is wrong and has to be replaced by 5S, because the ethynyl group has the priority over the tertiary bridgehead carbon atom.
10. Frackenpohl, J.; Hoffmann, H. M. R.: Synthesis of Enantiopure 3-Quinuclidinone Analogues with Three Stereogenic Centers: (1S,2R,4S)-and (1S,2S,4S)-2-(Hydroxymethyl)-1-azabicyclo-[2.2.2]octan-5-one and Stereocontrol of Nucleophilic Addition to the Carbonyl Group. J. Org. Chem. 65 (2000) 3982-3996.
11. Sheldrick, G. M.: Phase annealing in SHELXS-90. Direct methods for larger structures. Acta Crystallogr. A46 (1990) 467-473.
12. Sheldrick, G. M.: SHELXL-93. Program for the Refinement of Crystal Structures. University of Göttingen, Germany 1993.
13. Spek, A. L.: PLATON, an integrated tool for the analysis of the results of a single crystal structure determination. Acta Crystallogr. Suppl. A46 (1990) C-34.