Ruthenium-Catalyzed Enantioselective Carbon-Carbon Bond Forming Reaction via Allenylidene-Ene Process: Synthetic Approach to Chiral Heterocycles Such As Chromane, Thiochromane, and 1,2,3,4-Tetrahydroquinoline Derivatives
Koji Fukamizu; Yoshihiro Miyake; Yoshiaki Nishibayashi; Journal of the American Chemical Society 130 (2008) 10498–10499; doi:10.1021/ja8038745

data_4108186
_publ_section_title
;
 Ruthenium-Catalyzed Enantioselective Carbon-Carbon Bond Forming Reaction
 via Allenylidene-Ene Process: Synthetic Approach to Chiral Heterocycles
 Such As Chromane, Thiochromane, and 1,2,3,4-Tetrahydroquinoline
 Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10498
_journal_page_last               10499
_journal_paper_doi               10.1021/ja8038745
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C23 H17 Cl O '
_chemical_formula_sum            'C23 H17 Cl O'
_chemical_formula_weight         344.84
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            12
_cell_length_a                   9.9845(9)
_cell_length_b                   20.7418(15)
_cell_length_c                   25.4506(19)
_cell_measurement_reflns_used    22530
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     5270.7(7)
_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    SHELXS97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.994
_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  0.306
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            82121
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       needle
_exptl_crystal_F_000             2160.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.46
_refine_diff_density_min         -1.50
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  5368 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_coef       201(104)
_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     729
_refine_ls_number_reflns         12013
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0011Fo^2^ + 0.1465\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2058
_reflns_number_gt                2623
_reflns_number_total             12013
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja8038745-file004_3.cif
_cod_data_source_block           '_3k'
_cod_original_formula_sum        'C23 H17 Cl O '
_cod_database_code               4108186