Efficient Remote Axial-to-Central Chirality Transfer in Enantioselective SmI~2~-Mediated Reductive Coupling of Aldehydes with Crotonates of Atropisomeric 1-Naphthamides
Yan Zhang; Yongqiang Wang; Wei-Min Dai; Journal of Organic Chemistry 71 (2006) 2445–2455; doi:10.1021/jo0526486

data_4021586
_publ_contact_author_email       chdai@ust.hk
_publ_contact_author_fax         +852-23581594
_publ_contact_author_name        'Dr. Wei-Min Dai'
_publ_contact_author_phone       +852-23587365
_publ_section_title
;
 Efficient Remote Axial-to-Central Chirality Transfer in
 Enantioselective SmI~2~-Mediated Reductive Coupling of
 Aldehydes with Crotonates of Atropisomeric 1-Naphthamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2445
_journal_page_last               2455
_journal_paper_doi               10.1021/jo0526486
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C30 H39 N O6 '
_chemical_formula_sum            'C30 H39 N O6'
_chemical_formula_weight         509.64
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             2005-11-24
_audit_creation_method           'by CrystalStructure 3.7.0'
_cell_angle_alpha                90.0000
_cell_angle_beta                 113.3060(10)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.0513(9)
_cell_length_b                   14.5754(9)
_cell_length_c                   15.3593(9)
_cell_measurement_reflns_used    2246
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      20.8
_cell_measurement_theta_min      2.5
_cell_volume                     2889.0(3)
_computing_cell_refinement       PROCESS
_computing_data_collection       PROCESS
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20598
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         27.32
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.28
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  7296 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.036(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     668
_refine_ls_number_reflns         10022
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0001Fo^2^ + 0.9000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                7574
_reflns_number_total             12722
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo0526486si20051227_023828.cif
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C30 H39 N O6 '
_cod_database_code               4021586