Chiral Phosphoramide-Catalyzed Enantioselective Addition of Allylic Trichlorosilanes to Aldehydes. Preparative and Mechanistic Studies with Monodentate Phosphorus-Based Amides
Scott E. Denmark; Jiping Fu; Diane M. Coe; Xiping Su; Norman E. Pratt; Brian D. Griedel; Journal of Organic Chemistry 71 (2006) 1513–1522; doi:10.1021/jo052202p

data_4021500
_publ_section_title
;
 Chiral Phosphoramide-Catalyzed Enantioselective Addition
 of Allylic Trichlorosilanes to Aldehydes. Preparative and
 Mechanistic Studies with Monodentate Phosphorus-Based Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1513
_journal_page_last               1522
_journal_paper_doi               10.1021/jo052202p
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        XS-IV-83R
_chemical_formula_moiety         C28H28N3OP
_chemical_formula_sum            'C18 H28 N3 O P'
_chemical_formula_weight         333.40
_chemical_name_common            Endo-Proline-phosphoramide(3,5-di-Me-Ph).
_space_group_IT_number           4
_symmetry_cell_setting           triclinic
_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
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.000(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3934(5)
_cell_length_b                   9.9221(8)
_cell_length_c                   28.137(2)
_cell_measurement_reflns_used    2011
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      4
_cell_volume                     1784.9(2)
_computing_cell_refinement       'SAINT (Siemens, 1994)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        'SAINT (Siemens, 1994)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1994)'
_computing_publication_material  'CIFTAB (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXTL (Siemens, 1994)'
_computing_structure_solution    'SHELXTL (Siemens, 1994)'
_diffrn_ambient_temperature      198(2)
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_refln_elapsed_time       0.1667
_diffrn_reflns_av_R_equivalents  0.1229
_diffrn_reflns_av_sigmaI/netI    0.2056
_diffrn_refln_scan_width         0.3
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11596
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.45
_diffrn_standards_decay_%        0.8
_diffrn_standards_interval_time  360
_diffrn_standards_number         130
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       columnar
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(26)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.200
_refine_ls_goodness_of_fit_obs   1.288
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6725
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.204
_refine_ls_restrained_S_obs      1.288
_refine_ls_R_factor_all          0.2487
_refine_ls_R_factor_obs          0.1163
_refine_ls_shift/esd_max         -0.003
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+5.4327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2304
_refine_ls_wR_factor_obs         0.1652
_reflns_number_observed          3189
_reflns_number_total             6730
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jo052202psi20051024_043047.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+5.4327P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+5.4327P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 1'
_cod_database_code               4021500