Regioselectivity switch in chiral amine-catalysed asymmetric addition of aldehydes to reactive enals
Taichi Kano; Hiroki Maruyama; Ryu Sakamoto; Keiji Maruoka; Chem.Commun. 51 (2015) 10062–; doi:10.1039/C5cc02438B

data_7117278
_publ_section_title
;
 Regioselectivity switch in chiral amine-catalysed asymmetric addition of
 aldehydes to reactive enals
;
_journal_name_full               Chem.Commun.
_journal_page_first              10062
_journal_paper_doi               10.1039/C5cc02438B
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_sum            'C39 H42 Cl2 N O6 P'
_chemical_formula_weight         722.61
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-03-11 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.356(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.921(3)
_cell_length_b                   16.320(4)
_cell_length_c                   11.549(3)
_cell_measurement_reflns_used    1473
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      25.4
_cell_volume                     1854.5(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14750
_diffrn_reflns_theta_full        68.32
_diffrn_reflns_theta_max         68.32
_diffrn_reflns_theta_min         6.66
_exptl_absorpt_coefficient_mu    2.361
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_correction_T_min  0.8336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB(Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.024(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         6264
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.8114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                5411
_reflns_number_total             6264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02438b2.cif
_cod_data_source_block           4310
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7117278