Enantioselective Ring-Opening Reactions of Racemic Ethynyl Epoxides via Copper-Allenylidene Intermediates: Efficient Approach to Chiral β-Amino Alcohols
Gaku Hattori; Akiko Yoshida; Yoshihiro Miyake; Yoshiaki Nishibayashi; Journal of Organic Chemistry 74 (2009) 7603–7607; doi:10.1021/jo901064n

data_4024904
_publ_section_title
;
Enantioselective Ring-Opening Reactions of Racemic Ethynyl Epoxides via
Copper-Allenylidene Intermediates: Efficient Approach to Chiral \b-Amino
Alcohols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7603
_journal_page_last               7607
_journal_paper_doi               10.1021/jo901064n
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C24 H20 F3 N O3 S '
_chemical_formula_sum            'C24 H20 F3 N O3 S'
_chemical_formula_weight         459.48
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_date             2008-11-20
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 126.069(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   24.413(3)
_cell_length_b                   5.8853(9)
_cell_length_c                   19.075(2)
_cell_measurement_reflns_used    6378
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     2215.3(5)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_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 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.101
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10920
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             952.00
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.06
_refine_diff_density_min         -0.95
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1829 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_extinction_coef       22(11)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4100
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0001Fo^2^ + 0.6130\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                1929
_reflns_number_total             4100
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo901064n_si_002.cif
_cod_data_source_block           '_GH-Ts-4'
_cod_original_formula_sum        'C24 H20 F3 N O3 S '
_cod_database_code               4024904