Enantioselective, (-)-sparteine-mediated deprotonation of geranyl and neryl N,N-diisopropylcarbamate: Configurational stability of the intermediate lithium compounds

Tetrahedron

Volumn 61, Issue 13, 2005, Pages 3281-3287

  Zeng, Wenbin ^a   Fröhlich, Roland ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

( ) Sparteine; Allyllithium; Asymmetric deprotonation; Stereoselectivity

Indexed keywords

CARBAMIC ACID DERIVATIVE; CHLOROTRIMETHYLSILANE; GERANYL N,N DIISOPROPYLCARBAMATE; LITHIUM DERIVATIVE; NERYL N,N DIISOPROPYLCARBAMATE; SPARTEINE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; EPIMERIZATION; ISOMERIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; SUBSTITUTION REACTION; TEMPERATURE SENSITIVITY;

EID: 14844289573     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.100     Document Type: Article

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39. -3, hydrogens calculated and refined as riding atoms. Data set was collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Meth. Enzymol., 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-252331. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk ].
40. -3, hydrogens calculated and refined as riding atoms. Data set was collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Meth. Enzymol., 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-252331. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk ].
41. -3, hydrogens calculated and refined as riding atoms. Data set was collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Meth. Enzymol., 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-252331. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk ].
42. -3, hydrogens calculated and refined as riding atoms. Data set was collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Meth. Enzymol., 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-252331. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk ].
43. -3, hydrogens calculated and refined as riding atoms. Data set was collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Meth. Enzymol., 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-252331. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk ].
44. -3, hydrogens calculated and refined as riding atoms. Data set was collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Meth. Enzymol., 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-252331. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk ].
45. -3, hydrogens calculated and refined as riding atoms. Data set was collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Meth. Enzymol., 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-252331. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk ].
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