Enantioselective Synthesis of Tertiary Alcohols through a Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrroles with α-Ketoesters
Gonzalo Blay; Isabel Fernández; M. Carmen Muñoz; José R. Pedro; Alejandro Recuenco; Carlos Vila; Journal of Organic Chemistry 76 (2011) 6286–6294; doi:10.1021/jo2010704

data_4026498
_publ_section_title
;
 Enantioselective Synthesis of Tertiary Alcohols through a
 Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrroles with
 \a-Ketoesters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6286
_journal_page_last               6294
_journal_paper_doi               10.1021/jo2010704
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H12 Cl N O5'
_chemical_formula_weight         285.68
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 104.521(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6560(4)
_cell_length_b                   5.9190(2)
_cell_length_c                   13.1680(5)
_cell_measurement_reflns_used    200
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      15
_cell_volume                     653.11(5)
_computing_cell_refinement       'HKL DENZO'
_computing_data_collection       COLLECT
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0104
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3005
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'empirical absorption correction:XABS2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.0311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                2564
_reflns_number_total             3005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2010704_si_002.cif
_cod_data_source_block           ja613
_cod_original_cell_volume        653.11(4)
_cod_database_code               4026498