Enantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes
Chu-Hung Wei; Subramaniyan Mannathan; Chien-Hong Cheng; Journal of the American Chemical Society 133 (2011) 6942–6944; doi:10.1021/ja201827j

data_4106124
_publ_section_title
;
 Enantioselective Synthesis of \b-Substituted Cyclic Ketones via
 Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6942
_journal_page_last               6944
_journal_paper_doi               10.1021/ja201827j
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration S
_chemical_formula_sum            'C20 H19.5 Cl2 N O1.25'
_chemical_formula_weight         364.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.828(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   38.458(2)
_cell_length_b                   5.8962(2)
_cell_length_c                   18.4814(14)
_cell_measurement_reflns_used    2702
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      77.4183
_cell_measurement_theta_min      4.3524
_cell_volume                     3803.4(5)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7696
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         4.36
_exptl_absorpt_coefficient_mu    3.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             1524
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.026(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         4988
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0799P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                4046
_reflns_number_total             4988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja201827j_si_002.cif
_cod_data_source_block           ic14429
_cod_original_cell_volume        3803.5(4)
_cod_original_formula_sum        'C20 H19.50 Cl2 N O1.25'
_cod_database_code               4106124