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_4107492
_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_absolute_configuration syn
_chemical_formula_moiety
'2 C19 H25 O4 P S, C8 H12, Rh 1+, C F3 S O3 1-'
_chemical_formula_sum            'C47 H62 F3 O11 P2 Rh S3'
_chemical_formula_weight         1121.00
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5530(6)
_cell_length_b                   10.5530(6)
_cell_length_c                   50.011(2)
_cell_measurement_reflns_used    5484
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1
_cell_volume                     5569.5(5)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w-scans
_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  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_number            20034
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'DENZO and Scalepack (Otwinoski and Minor, 1997)'
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       plates
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.284
_refine_diff_density_min         -1.790
_refine_diff_density_rms         0.155
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     518
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1078
_refine_ls_shift/su_max          0.071
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+48.7689P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2592
_refine_ls_wR_factor_ref         0.2740
_reflns_number_gt                3881
_reflns_number_total             5408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja710862u-file002.cif
_cod_data_source_block           rhcod1
_cod_database_code               4107492