Diastereo- and Enantioselective Hydrogenative Aldol Coupling of Vinyl Ketones: Design of Effective Monodentate TADDOL-Like Phosphonite Ligands
Cisco Bee; Soo Bong Han; Abbas Hassan; Hiroki Iida; Michael J. Krische; Journal of the American Chemical Society 130 (2008) 2746–2747; doi:10.1021/ja710862u

data_4107491
_publ_section_title
;
 Diastereo- and Enantioselective Hydrogenative Aldol Coupling of Vinyl
 Ketones: Design of Effective Monodentate TADDOL-Like Phosphonite Ligands
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2746
_journal_page_last               2747
_journal_paper_doi               10.1021/ja710862u
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C14 H13 Br N O4'
_chemical_formula_weight         339.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.920(5)
_cell_angle_beta                 94.895(5)
_cell_angle_gamma                96.313(5)
_cell_formula_units_Z            2
_cell_length_a                   5.0572(7)
_cell_length_b                   11.6708(14)
_cell_length_c                   13.3628(15)
_cell_measurement_temperature    293(2)
_cell_volume                     709.22(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3526
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    2.910
_exptl_absorpt_correction_T_max  0.8925
_exptl_absorpt_correction_T_min  0.5183
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.814
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       0.000(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.340
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.340
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0759
_refine_ls_shift/su_max          1.438
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+1.7279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1876
_reflns_number_gt                2739
_reflns_number_total             3526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja710862u-file001.cif
_cod_data_source_block           cb1x2
_cod_original_cell_volume        709.22(15)
_cod_database_code               4107491