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_4107493
_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            'C22 H19 Br N2 O7'
_chemical_formula_weight         503.30
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.179(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3647(3)
_cell_length_b                   9.5326(5)
_cell_length_c                   15.7688(7)
_cell_measurement_temperature    153(2)
_cell_volume                     1089.62(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14494
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_T_max  0.8452
_exptl_absorpt_correction_T_min  0.6757
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(5)
_refine_ls_extinction_coef       0.0000(7)
_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   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4827
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          3.944
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0173P)^2^+0.3252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0580
_reflns_number_gt                4380
_reflns_number_total             4827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja710862u-file005.cif
_cod_data_source_block           no2br
_cod_database_code               4107493