anti-Selective, Catalytic Asymmetric Vinylogous Mukaiyama Mannich Reactions of Pyrrole-Based Silyl Dienolates with N-Aryl Aldimines
Claudio Curti; Lucia Battistini; Beatrice Ranieri; Giorgio Pelosi; Gloria Rassu; Giovanni Casiraghi; Franca Zanardi; Journal of Organic Chemistry 76 (2011) 2248–2252; doi:10.1021/jo1021234

data_4026153
_publ_section_title
;
 anti-Selective, Catalytic Asymmetric Vinylogous Mukaiyama Mannich
 Reactions of Pyrrole-Based Silyl Dienolates with N-Aryl Aldimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2248
_journal_page_last               2252
_journal_paper_doi               10.1021/jo1021234
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C23 H26 N2 O4'
_chemical_formula_weight         394.46
_chemical_name_systematic
;
(R)-5-(N-tert-Butoxycarbonyl)-[(S)-(2-methoxyphenylamino)-
(phenyl)methyl]-1H-pirrol-2(5H)one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.7109(7)
_cell_length_b                   17.8216(10)
_cell_length_c                   19.5965(11)
_cell_measurement_temperature    293(2)
_cell_volume                     4439.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37759
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS (1999)'
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.822
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.822
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0510
_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^)+(0.1226P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1872
_reflns_number_gt                2232
_reflns_number_total             5126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1021234_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4026153