Addition of optically pure H-phosphinate to ketones: selectivity, stereochemistry and mechanism.
Sun, Yong-Ming; Xin, Nana; Xu, Zhong-Yuan; Liu, Li-Juan; Meng, Fan-Jie; Zhang, He; Fu, Bao-Ci; Liang, Qiu-Ju; Zheng, Hong-Xing; Sun, Li-Jun; Zhao, Chang-Qiu; Han, Li-Biao; Organic & biomolecular chemistry 12 (2014) 9457–; doi:10.1039/c4ob01574f

data_7154152
_publ_section_title
;
 Addition of optically pure H-phosphinate to ketones: selectivity,
 stereochemistry and mechanism.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9457
_journal_paper_doi               10.1039/c4ob01574f
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C25 H30 N0 O4 P'
_chemical_formula_weight         425.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_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                 92.5340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.436(13)
_cell_length_b                   5.7781(7)
_cell_length_c                   15.9687(16)
_cell_measurement_temperature    298(2)
_cell_volume                     1146.3(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1238
_diffrn_reflns_av_sigmaI/netI    0.1382
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5868
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9392
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.187
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1811
_refine_ls_R_factor_gt           0.1367
_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3229
_refine_ls_wR_factor_ref         0.3557
_reflns_number_gt                2107
_reflns_number_total             3683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01574f2.cif
_cod_data_source_block           121201b
_cod_depositor_comments
'Adding full bibliography for 7154151--7154157.cif.'
_cod_database_code               7154152