Bifuctional Amino-Squaramides Catalyzed Asymmetric Spiroannulation Cascades with Aliphatic β,γ-Unsaturated α-Keto Esters: Controlling an Aldehyde Enolate
Xiaoqin Wang; Weijun Yao; Zhihui Yao; Cheng Ma; Journal of Organic Chemistry 77 (2012) 2959–2965; doi:10.1021/jo202633c

data_4027069
_publ_section_title
;
 Bifuctional Amino-Squaramides Catalyzed Asymmetric Spiroannulation
 Cascades with Aliphatic \b,\g-Unsaturated \a-Keto Esters: Controlling an
 Aldehyde Enolate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2959
_journal_page_last               2965
_journal_paper_doi               10.1021/jo202633c
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 O6'
_chemical_formula_sum            'C22 H24 O6'
_chemical_formula_weight         384.41
_space_group_IT_number           145
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   9.3573(2)
_cell_length_b                   9.3573(2)
_cell_length_c                   40.4414(15)
_cell_measurement_reflns_used    11086
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3817
_cell_measurement_theta_min      3.2757
_cell_volume                     3066.61(15)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            28051
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.7960
_exptl_absorpt_correction_T_min  0.7645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Oxford Diffraction, 2010) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack (1983), 3124 Friedel pairs'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.0060(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         6810
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0896
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1670P)^2^+2.7951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2641
_refine_ls_wR_factor_ref         0.2690
_reflns_number_gt                6307
_reflns_number_total             6810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202633c_si_002.cif
_cod_data_source_block           110712_wxq308
_cod_database_code               4027069