Cationic Rh(I)/modified-BINAP-catalyzed reactions of carbonyl compounds with 1,6-diynes leading to dienones and ortho-functionalized aryl ketones.
Tanaka, Ken; Otake, Yousuke; Wada, Azusa; Noguchi, Keiichi; Hirano, Masao; Organic letters 9 (2007) 2203–2206; doi:10.1021/ol0707721

data_1505415
_publ_section_title
;
 Cationic Rh(I)/modified-BINAP-catalyzed reactions of carbonyl compounds
 with 1,6-diynes leading to dienones and ortho-functionalized aryl
 ketones.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2203
_journal_page_last               2206
_journal_paper_doi               10.1021/ol0707721
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C23 H25 N O3 S'
_chemical_formula_sum            'C23 H25 N O3 S'
_chemical_formula_weight         395.50
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-09-11
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.462(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3244(9)
_cell_length_b                   16.2185(13)
_cell_length_c                   23.6410(17)
_cell_measurement_reflns_used    33466
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.7
_cell_volume                     4341.9(6)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            39958
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    1.500
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3979
_refine_ls_number_restraints     134
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1387P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2237
_refine_ls_wR_factor_ref         0.2381
_reflns_number_gt                2269
_reflns_number_total             3979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0707721si20070330_024207.cif
_cod_data_source_block           shelxl
_cod_database_code               1505415