Organocatalytic Enantioselective Synthesis of Both Diastereomers of α-Hydroxyphosphinates
Sampak Samanta; Sandun Perera; Cong-Gui Zhao; Journal of Organic Chemistry 75 (2010) 1101–1106; doi:10.1021/jo9022099

data_4025223
_publ_contact_author_address
;
    Department of Chemistry,
    The University of Texas,
    One UTSA Circle, San Antonio,
    Texas 78249-0621, USA
;
_publ_contact_author_email
;
Edward.Tiekink@utsa.edu
;
_publ_contact_author_fax         ' 1 210 458 7428 '
_publ_contact_author_name        ' Dr ERT Tiekink '
_publ_contact_author_phone       ' 1 210 458 5469 '
_publ_section_title
;
 Organocatalytic Enantioselective Synthesis of Both Diastereomers of
 \a-Hydroxyphosphinates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1101
_journal_page_last               1106
_journal_paper_doi               10.1021/jo9022099
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C18 H22 Br O5 P'
_chemical_formula_sum            'C18 H22 Br O5 P'
_chemical_formula_weight         429.24
_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
_cell_angle_beta                 104.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.140(2)
_cell_length_b                   5.7779(12)
_cell_length_c                   16.691(3)
_cell_measurement_reflns_used    2824
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      2.5
_cell_volume                     945.5(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  AFC12\K/SATURN724
_diffrn_measurement_method       \w
_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  0.042
_diffrn_reflns_av_sigmaI/netI    0.058
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6979
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.283
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.37
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                3382
_reflns_number_total             3568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9022099_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4025223