A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes.
Witten, Michael R.; Jacobsen, Eric N.; Organic letters 17 (2015) 2772–2775; doi:10.1021/acs.orglett.5b01193

data_1519697
_publ_section_title
;
 A Simple Primary Amine Catalyst for Enantioselective \a-Hydroxylations
 and \a-Fluorinations of Branched Aldehydes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2772
_journal_page_last               2775
_journal_paper_doi               10.1021/acs.orglett.5b01193
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H10 Br F O'
_chemical_formula_weight         233.08
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_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
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_cell_length_c                   10.972(4)
_cell_measurement_reflns_used    7469
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.06
_cell_volume                     453.4(3)
_computing_cell_refinement       'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
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_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
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_diffrn_measured_fraction_theta_max 0.987
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;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi 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  0.0371
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10136
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.348
_diffrn_reflns_theta_min         1.859
_exptl_absorpt_coefficient_mu    4.496
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_exptl_absorpt_correction_T_min  0.5084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 805 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0187
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+0.0210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0456
_refine_ls_wR_factor_ref         0.0465
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                1898
_reflns_number_total             2018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01193_si_004.cif
_cod_data_source_block           fluoro-p-bromo
_cod_depositor_comments
'Adding full bibliography for 1519696--1519698.cif.'
_cod_database_code               1519697
_shelx_estimated_absorpt_t_min   0.572
_shelx_estimated_absorpt_t_max   0.662
_shelxl_version_number           2014/6
_shelx_res_checksum              99431
_shelx_hkl_checksum              66120