Highly Regio-, Diastereo-, and Enantioselective 1,6- and 1,8-Additions of Azlactones to Di- and Trienyl N-Acylpyrroles
Daisuke Uraguchi; Ken Yoshioka; Yusuke Ueki; Takashi Ooi; Journal of the American Chemical Society 134 (2012) 19370–19373; doi:10.1021/ja310209g

data_4118934
_publ_section_title
;
 Highly Regio-, Diastereo-, and Enantioselective 1,6- and 1,8-Additions of
 Azlactones to Di- and Trienyl N-Acylpyrroles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19370
_journal_page_last               19373
_journal_paper_doi               10.1021/ja310209g
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C38 H39 Cl N2 O6'
_chemical_formula_weight         655.16
_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                   10.008(3)
_cell_length_b                   10.996(3)
_cell_length_c                   30.926(10)
_cell_measurement_temperature    113(2)
_cell_volume                     3403.3(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  VariMax
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            28394
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9762
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       plate
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1871
_reflns_number_gt                5717
_reflns_number_total             7756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310209g_si_002.cif
_cod_data_source_block           8
_cod_original_formula_sum        'C38 H39 Cl1 N2 O6'
_cod_database_code               4118934