Synthesis of stereohomogeneous cyclopropanecarbaldehydes and cyclopropyl ketones by cycloalkylation of 4-hydroxy-1-alkenyl carbamates

Angewandte Chemie - International Edition

Volumn 43, Issue 48, 2004, Pages 6667-6669

  Kalkofen, Rainer ^a   Brandau, Sven ^a   Wibbeling, Birgit ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Asymmetric synthesis; Cyclization; Cyclopropanes; Synthetic methods

Indexed keywords

ALDEHYDES; ALKYLATION; KETONES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLOALKYLATION; CYCLOPROPANE CARBALDEHYDES; CYCLOPROPYL KETONES;

AROMATIC COMPOUNDS;

4 HYDROXYCARBAMATE DERIVATIVE; ALDEHYDE; CARBAMIC ACID DERIVATIVE; CARBAMOYL DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYCLOPROPANECARBALDEHYDE DERIVATIVE; FUNCTIONAL GROUP; KETONE; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLOALKYLATION; ENANTIOSELECTIVITY; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 10944224965     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461136     Document Type: Article

References (40)

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30. -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 (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-240544 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK: fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
31. -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 (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-240544 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK: fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
32. -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 (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-240544 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK: fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
33. -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 (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-240544 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK: fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
34. -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 (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-240544 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK: fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
35. -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 (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-240544 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK: fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
36. -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 (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, 1997). CCDC-240544 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK: fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
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