Enhanced Stereoselectivity of a Cu(II) Complex Chiral Auxiliary in the Synthesis of Fmoc-l-γ-carboxyglutamic Acid
Daniel J. Smith; Glenn P. A. Yap; James A. Kelley; Joel P. Schneider; Journal of Organic Chemistry 76 (2011) 1513–1520; doi:10.1021/jo101940k

data_4026098
_publ_section_title
;
 Enhanced Stereoselectivity of a Cu(II) Complex Chiral Auxiliary in the
 Synthesis of Fmoc-l-\g-carboxyglutamic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1513
_journal_page_last               1520
_journal_paper_doi               10.1021/jo101940k
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C28 H27 N3 Ni O3 S'
_chemical_formula_weight         544.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.108(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.428(5)
_cell_length_b                   8.062(4)
_cell_length_c                   29.581(8)
_cell_measurement_reflns_used    955
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.62
_cell_volume                     2472.8(18)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       \w
_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  0.0825
_diffrn_reflns_av_sigmaI/netI    0.1030
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            32913
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         0.69
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  0.9519
_exptl_absorpt_correction_T_min  0.6528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881: 5685 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.028(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         12271
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                7776
_reflns_number_total             12271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101940k_si_001.cif
_cod_data_source_block           joes005
_cod_database_code               4026098