Asymmetric Propargylboration of Aldimines and Ketimines with the Borabicyclo[3.3.2]decanes: Novel Entries to Allenyl Carbinamines, Amino Acids, and Their α-Methyl Counterparts.
Alicea-Matías, Eyleen; Soderquist, John A.; Organic letters 19 (2017) 336–339; doi:10.1021/acs.orglett.6b03506

data_1555994
_publ_section_title
;
 Asymmetric Propargylboration of Aldimines and Ketimines with the
 Borabicyclo[3.3.2]decanes: Novel Entries to Allenyl Carbinamines, Amino
 Acids, and Their \a-Methyl Counterparts.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              336
_journal_page_last               339
_journal_paper_doi               10.1021/acs.orglett.6b03506
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C19 H27 Br N O2 Si'
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_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5667(19)
_cell_length_b                   11.1762(16)
_cell_length_c                   18.221(3)
_cell_measurement_reflns_used    3151
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.88
_cell_volume                     2151.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9532
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.056
_diffrn_reflns_theta_min         2.235
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       plate
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.517
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details
; 
 Flack x determined using 1237 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.053(10)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0860P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3446
_reflns_number_total             4196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03506_si_001.cif
_cod_data_source_block           matias01
_cod_database_code               1555994
_shelx_estimated_absorpt_t_min   0.598
_shelx_estimated_absorpt_t_max   0.858
_shelxl_version_number           2013-3
_shelx_res_checksum              30620
_shelx_hkl_checksum              66198