Morita-Baylis-Hillman adducts as effective dipolarophiles in Copper(I)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides: asymmetric construction of pyrrolidine derivatives containing quaternary stereogenic center
Huai-Long Teng; He Huang; Hai-Yan Tao; Chun-Jiang Wang; Chem.Commun. 47 (2011) 5494–; doi:10.1039/c1cc11138h

data_7106376
_publ_section_title
;
 Morita-Baylis-Hillman adducts as effective dipolarophiles in
 Copper(I)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides:
 asymmetric construction of pyrrolidine derivatives containing quaternary
 stereogenic center
;
_journal_name_full               Chem.Commun.
_journal_page_first              5494
_journal_paper_doi               10.1039/c1cc11138h
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration 7R,8S,10R
_chemical_formula_sum            'C32 H32 Cl N O7'
_chemical_formula_weight         578.04
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                   19.401(3)
_cell_length_b                   24.000(3)
_cell_length_c                   6.6143(9)
_cell_measurement_reflns_used    5228
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.61
_cell_measurement_theta_min      2.26
_cell_volume                     3079.8(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            17928
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_correction_T_min  0.9474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       0.0049(3)
_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   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.7880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                4817
_reflns_number_total             6359
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11138h.txt
_cod_data_source_block           9
_cod_original_sg_symbol_H-M      P2(1)2(1)2
_cod_database_code               7106376