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_4108184
_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         'C19 H16 O '
_chemical_formula_sum            'C19 H16 O'
_chemical_formula_weight         260.33
_space_group_IT_number           4
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.330(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.4671(9)
_cell_length_b                   6.2402(8)
_cell_length_c                   12.0915(12)
_cell_measurement_reflns_used    4931
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     678.08(13)
_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 0.970
_diffrn_measured_fraction_theta_max 0.972
_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  0.043
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6726
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.711
_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    1.275
_exptl_crystal_description       plate
_exptl_crystal_F_000             276.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.91
_refine_diff_density_min         -0.72
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1347 Friedel Pairs'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2997
_refine_ls_R_factor_gt           0.0699
_refine_ls_shift/su_max          0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[3.4950\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                1893
_reflns_number_total             2997
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja8038745-file004_1.cif
_cod_data_source_block           '_4'
_cod_original_cell_volume        678.08(12)
_cod_original_formula_sum        'C19 H16 O '
_cod_database_code               4108184