3-Pyrrolidinecarboxylic Acid for Direct Catalytic Asymmetricanti-Mannich-Type Reactions of Unmodified Ketones
Haile Zhang; Maria Mifsud; Fujie Tanaka; Carlos F. Barbas; Journal of the American Chemical Society 128 (2006) 9630–9631; doi:10.1021/ja062950b

data_4110775
_publ_section_title
;
 3-Pyrrolidinecarboxylic Acid for Direct Catalytic
 Asymmetricanti-Mannich-Type Reactions of Unmodified Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9630
_journal_page_last               9631
_journal_paper_doi               10.1021/ja062950b
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C15 H21 N O4'
_chemical_formula_weight         279.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3458(11)
_cell_length_b                   15.312(3)
_cell_length_c                   18.622(4)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.80
_cell_measurement_theta_min      2.56
_cell_volume                     1524.3(5)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11267
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.2722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      0
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             600
_exptl_crystal_size_max          20.00
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0643P)^2^+0.2450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                2170
_reflns_number_total             2690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja062950bsi20060505_030030.cif
_cod_data_source_block           zpnp
_cod_database_code               4110775