Organocatalytic Asymmetric Decarboxylative Amination of β-Keto Acids: Access to Optically Active α-Amino Ketones and 1,2-Amino Alcohols.
Wei, Yi; Zhang, Heng-Xia; Zeng, Jun-Liang; Nie, Jing; Ma, Jun-An; Organic letters 19 (2017) 2162–2165; doi:10.1021/acs.orglett.7b00797

data_1545928
_publ_section_title
;
 Organocatalytic Asymmetric Decarboxylative Amination of \b-Keto Acids:
 Access to Optically Active \a-Amino Ketones and 1,2-Amino Alcohols.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2162
_journal_page_last               2165
_journal_paper_doi               10.1021/acs.orglett.7b00797
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H14 Cl N O'
_chemical_formula_weight         199.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7337(2)
_cell_length_b                   6.2908(2)
_cell_length_c                   33.7597(12)
_cell_measurement_reflns_used    2057
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      70.8810
_cell_measurement_theta_min      7.1410
_cell_volume                     1005.32(6)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            3070
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.056
_diffrn_reflns_theta_min         5.241
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.028(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0127P)^2^+1.4653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.614
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                1831
_reflns_number_total             1896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00797_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               1545928
_shelx_estimated_absorpt_t_min   0.518
_shelx_estimated_absorpt_t_max   0.555
_shelxl_version_number           2013-4
_shelx_res_checksum              47941
_shelx_hkl_checksum              55750