Synthesis of syn- and enantioenriched anti--amino alcohols by highly diastereoselective borono-Mannich allylation reactions
Pyne, Stephen G.; Chevis, Philip; Promchai, Thanika; Richardson, Christopher; Limtharakul, Thunwadee; Chemical Communications  (2022) –; doi:10.1039/D1CC06775C

data_7129588
_publ_section_title
;
 Synthesis of syn- and enantioenriched anti-&#xF062;-amino alcohols by
 highly diastereoselective borono-Mannich allylation reactions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06775C
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H23 N O'
_chemical_formula_sum            'C19 H23 N O'
_chemical_formula_weight         281.38
_chemical_melting_point          355
_chemical_name_common            (2R,3S)-3-(benzylamino)-1-phenylhex-5-en-2-ol
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-11 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.89740(10)
_cell_length_b                   10.1935(3)
_cell_length_c                   32.6734(11)
_cell_measurement_reflns_used    11229
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.1530
_cell_measurement_theta_min      2.3480
_cell_volume                     1631.11(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      294(2)
_diffrn_detector
'Hybrid Pixel Array Detector HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00-120.00  368
  2  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00 -60.00  368
  3  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00 150.00  368
  4  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00 150.00  368
  5  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00  30.00  368
  6  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00 -30.00  368
  7  \w    -74.00  36.00   0.50    7.00    --   20.00  54.00-150.00  220
  8  \w    -74.00 110.00   0.50    7.00    --   20.00  54.00  90.00  368
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0058268000
_diffrn_orient_matrix_UB_12      0.0039090000
_diffrn_orient_matrix_UB_13      0.0216607000
_diffrn_orient_matrix_UB_21      -0.1388567000
_diffrn_orient_matrix_UB_22      -0.0195163000
_diffrn_orient_matrix_UB_23      0.0011746000
_diffrn_orient_matrix_UB_31      0.0408342000
_diffrn_orient_matrix_UB_32      -0.0666537000
_diffrn_orient_matrix_UB_33      0.0009226000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            39780
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         2.093
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane and chloroform'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0380P)^2^+0.1337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3807
_reflns_number_total             4750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06775c2.cif
_cod_data_source_block           exp_198_pc
_cod_database_code               7129588
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C19 H22 N1 O1'
_chemical_oxdiff_usercomment     PC_3_25
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C5-C4
 1.46 with sigma of 0.01
 C5A-C4
 1.46 with sigma of 0.01
 C6A-C5A = C6-C5
 1.33 with sigma of 0.01
 N3-H3B
 0.9 with sigma of 0.02
3. Others
 Sof(H4BC)=Sof(H4BD)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=1-FVAR(1)
 Sof(H4AA)=Sof(H4AB)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(1)
 Sof(H3B)=1-FVAR(2)
 Sof(H3A)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4AA,H4AB), C4(H4BC,H4BD), C1B(H1BA,H1BB)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C5A(H5A), C3B(H3BA), C4B(H4B), C5B(H5B), C6B(H6BA), C7B(H7B),
 C2P(H2P), C3P(H3P), C4P(H4P), C5P(H5P), C6P(H6P)
4.d X=CH2 refined with riding coordinates:
 C6(H6A,H6B), C6A(H6AA,H6AB)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              24392
_olex2_exptl_crystal_mounting_method 'Mitegen mount + Paratone'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.070
_oxdiff_exptl_absorpt_empirical_full_min 0.950