Highly Diastereoselective Arylations of Substituted Piperidines
Stephanie Seel; Tobias Thaler; Keishi Takatsu; Cong Zhang; Hendrik Zipse; Bernd F. Straub; Peter Mayer; Paul Knochel; Journal of the American Chemical Society 133 (2011) 4774–4777; doi:10.1021/ja201008e

data_4105890
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universit\"at
Butenandtstra\&se 5-13 (Haus F)
D-81377 M\"unchen
Bundesrepublik Deutschland
;
_publ_contact_author_email       paul.knochel@cup.uni-muenchen.de
_publ_contact_author_fax         '+49 089-2180-77680'
_publ_contact_author_name        'Paul Knochel'
_publ_section_title
;
 Highly Diastereoselective Arylations of Substituted Piperidines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4774
_journal_page_last               4777
_journal_paper_doi               10.1021/ja201008e
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C20 H22 N2 O2 S'
_chemical_formula_sum            'C20 H22 N2 O2 S'
_chemical_formula_weight         354.467
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'P. Mayer'
_audit_block_code                C20H22N2O2S_oo206_knochel
_audit_creation_date
;
'Wed Nov 17 15:43:27 2010'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             17-Nov-10
_cell_angle_alpha                88.074(7)
_cell_angle_beta                 76.203(7)
_cell_angle_gamma                87.599(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4047(6)
_cell_length_b                   9.5212(9)
_cell_length_c                   13.7988(11)
_cell_measurement_reflns_used    1302
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.2067
_cell_measurement_theta_min      4.2776
_cell_volume                     943.66(14)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega  -96.00  -64.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.1546  179.0000 -120.0000 32

  2 omega  -18.00   88.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2483   77.0000 -180.0000 106

  3 omega  -10.00   88.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2483   77.0000  -60.0000 98

  4 omega  -48.00   43.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2483  -77.0000   60.0000 91

  5 omega  -45.00   -5.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2483  -77.0000   90.0000 40

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0236359230
_diffrn_orient_matrix_UB_12      0.0694207068
_diffrn_orient_matrix_UB_13      -0.0171564136
_diffrn_orient_matrix_UB_21      0.0957454004
_diffrn_orient_matrix_UB_22      -0.0207880834
_diffrn_orient_matrix_UB_23      -0.0109071988
_diffrn_orient_matrix_UB_31      -0.0043022172
_diffrn_orient_matrix_UB_32      -0.0179327827
_diffrn_orient_matrix_UB_33      -0.0489512151
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.1372
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4869
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         4.29
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.24751(19)
_exptl_crystal_description       platelet
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.831
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                1212
_reflns_number_total             2651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja201008e_si_008.cif
_cod_data_source_block           oo206
_cod_database_code               4105890