Bisoxazolidine-Catalyzed Enantioselective Alkynylation of Aldehydes
Christian Wolf; Shuanglong Liu; Journal of the American Chemical Society 128 (2006) 10996–10997; doi:10.1021/ja062711o

data_4110842
_publ_section_title
;
 Bisoxazolidine-Catalyzed Enantioselective Alkynylation of Aldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10996
_journal_page_last               10997
_journal_paper_doi               10.1021/ja062711o
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration '1R, 2S'
_chemical_formula_moiety         'C49 H53 Cl3 N4 O4'
_chemical_formula_sum            'C24.5 H24.5 Cl1.5 N2 O2'
_chemical_formula_weight         432.14
_chemical_name_common            Bisoxzaolidine
_chemical_name_systematic
;
 (1R,2S)-cis-1-amino-2-indanol derived bisoxazolidine
;
_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                90.00
_cell_angle_beta                 108.5190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9199(16)
_cell_length_b                   5.5487(5)
_cell_length_c                   23.585(2)
_cell_measurement_reflns_used    7830
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.41
_cell_volume                     2099.6(3)
_computing_molecular_graphics    'XSEED, L. Barbour (1999); http:\x-seed.net'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'SMART platform CCD, Siemens/Bruker'
_diffrn_measurement_method       'omega scans'
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0842
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18634
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9479
_exptl_absorpt_correction_T_min  0.9233
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       Block
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         9623
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0668P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                6475
_reflns_number_total             9623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja062711osi20060427_015821.cif
_cod_data_source_block           c:\docume~1\xm3\desktop\work\p21
_cod_original_formula_sum        'C24.50 H24.50 Cl1.50 N2 O2'
_cod_database_code               4110842