A New Family of Cinchona-Derived Amino Phosphine Precatalysts: Application to the Highly Enantio- and Diastereoselective Silver-Catalyzed Isocyanoacetate Aldol Reaction
Filippo Sladojevich; Andrea Trabocchi; Antonio Guarna; Darren J. Dixon; Journal of the American Chemical Society 133 (2011) 1710–1713; doi:10.1021/ja110534g

data_4105638
_publ_contact_author             'Darren J. Dixon'
_publ_contact_author_email       darren.dixon@chem.ox.ac.uk
_publ_section_title
;
 A New Family of Cinchona-Derived Amino Phosphine Precatalysts:
 Application to the Highly Enantio- and Diastereoselective
 Silver-Catalyzed Isocyanoacetate Aldol Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1710
_journal_page_last               1713
_journal_paper_doi               10.1021/ja110534g
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 Br1 N1 O3'
_chemical_formula_sum            'C17 H16 Br N O3'
_chemical_formula_weight         362.22
_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
_audit_creation_date             09-11-13
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                90
_cell_angle_beta                 90.8890(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2156(3)
_cell_length_b                   6.7637(2)
_cell_length_c                   11.1574(3)
_cell_measurement_reflns_used    1864
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     770.83(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11714
_diffrn_reflns_theta_full        26.923
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         5.119
_diffrn_standards_decay_%        -
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.678
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.69
_refine_ls_abs_structure_details 'Flack (1983), 1469 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.008(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.000608
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 26.4 41.9 25.3 11.4 3.21 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0699
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0699
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3152
_reflns_number_total             3369
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.50
_oxford_diffrn_Wilson_scale      2.05
_oxford_refine_ls_r_factor_ref   0.0322
_oxford_refine_ls_scale          0.6870(13)
_oxford_reflns_number_all        3363
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '8071602 005djd09'
_cod_data_source_file            ja110534g_si_003.cif
_cod_data_source_block           7t
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C17 H16 Br1 N1 O3'
_cod_database_code               4105638