Enantioselective allylic amination of MBH carbonates catalyzed by novel chiral 4-dialkylaminopyridine catalysts
Ma, Gaoyuan; Sibi, Mukund P.; Org. Chem. Front. 1 (2014) 1152–; doi:10.1039/C4QO00210E

data_1553033
_publ_section_title
;
 Enantioselective allylic amination of MBH carbonates catalyzed by novel
 chiral 4-dialkylaminopyridine catalysts
;
_journal_issue                   10
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              1152
_journal_paper_doi               10.1039/C4QO00210E
_journal_volume                  1
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H28 N4 O'
_chemical_formula_sum            'C21 H28 N4 O'
_chemical_formula_weight         352.47
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4860)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   13.2040(2)
_cell_length_b                   13.2040(2)
_cell_length_c                   11.50280(10)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.22
_cell_measurement_theta_min      3.87
_cell_volume                     1736.78(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18957
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         3.866
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0468 before and 0.0361 after correction.
The Ratio of minimum to maximum transmission is 0.9045.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.011
_exptl_crystal_description       plate
_exptl_crystal_F_000             570
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.086
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+0.1656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0582
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3910
_reflns_number_total             3975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4qo00210e2.cif
_cod_data_source_block           jxd2_sq
_cod_original_cell_volume        1736.78(5)
_cod_database_code               1553033
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              18342
_shelx_hkl_checksum              11561
_shelx_fab_checksum              34921
_olex2_submission_special_instructions 'No special instructions were received'