Asymmetric Synthesis of β-Hydroxy-α-amino Phosphonic Acid Derivatives via Organocatalytic Direct Aldol Reaction of α-Isothiocyanato Phosphonates with Aldehydes
Wen-Yong Han; Jian-Qiang Zhao; Zhi-Jun Wu; Xiao-Mei Zhang; Wei-Cheng Yuan; Journal of Organic Chemistry 78 (2013) 10541–10547; doi:10.1021/jo401779x

data_4028685
_publ_section_title
;
 Asymmetric Synthesis of \b-Hydroxy-\a-amino Phosphonic Acid Derivatives
 via Organocatalytic Direct Aldol Reaction of \a-Isothiocyanato
 Phosphonates with Aldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10541
_journal_page_last               10547
_journal_paper_doi               10.1021/jo401779x
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H22 N O4 P S'
_chemical_formula_weight         391.41
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_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
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_cell_length_b                   16.4155(18)
_cell_length_c                   19.6133(12)
_cell_measurement_reflns_used    1912
_cell_measurement_temperature    290(2)
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_cell_measurement_theta_min      3.1096
_cell_volume                     1962.0(3)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
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_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9091
_exptl_absorpt_correction_T_min  0.8928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             824
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_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.233
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_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(15)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1580
_reflns_number_gt                2434
_reflns_number_total             3714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401779x_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4028685