Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with Alkylidenemalonates
Qin Liu; Stéphane Perreault; Tomislav Rovis; Journal of the American Chemical Society 130 (2008) 14066–14067; doi:10.1021/ja805680z

data_4108557
_publ_section_title
;
 Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with
 Alkylidenemalonates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14066
_journal_page_last               14067
_journal_paper_doi               10.1021/ja805680z
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ab
_chemical_formula_sum            'C13 H19 O7'
_chemical_formula_weight         287.28
_chemical_name_systematic
;                                                                              
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;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9730(14)
_cell_length_b                   10.0535(15)
_cell_length_c                   15.128(2)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      60.42
_cell_measurement_theta_min      5.28
_cell_volume                     1364.7(3)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'MWPC area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19862
_diffrn_reflns_theta_full        60.02
_diffrn_reflns_theta_max         60.02
_diffrn_reflns_theta_min         7.23
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.8525
_exptl_absorpt_correction_T_min  0.8149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       'plate     '
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(18)
_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     182
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.1951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0796
_reflns_number_gt                1848
_reflns_number_total             1905
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja805680z_si_003.cif
_cod_data_source_block           csu
_cod_original_cell_volume        1364.7(4)
_cod_database_code               4108557