Domino Elimination/Nucleophilic Addition in the Synthesis of Chiral Pyrrolidines
Mari Fe Flores; Pilar García-García; Narciso M. Garrido; Isidro S. Marcos; Francisca Sanz-González; David Díez; Journal of Organic Chemistry 78 (2013) 7068–7075; doi:10.1021/jo400873c

data_4028424
_publ_contact_author_address
;
Departamento de Quimica Organica,
Facultad de Ciencias Quimicas,
Universidad de Salamanca,
37008-Salamanca. Spain
;
_publ_contact_author_email       ddm@usal.es
_publ_contact_author_fax         '0034 923294574'
_publ_contact_author_name        'David Diez Martin'
_publ_contact_author_phone       '0034 923294474'
_publ_section_title
;
 Domino Elimination/Nucleophilic Addition in the Synthesis of Chiral
 Pyrrolidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7068
_journal_page_last               7075
_journal_paper_doi               10.1021/jo400873c
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H24 F N O5 S'
_chemical_formula_sum            'C21 H24 F N O5 S'
_chemical_formula_weight         421.47
_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           'form.cif (version 2.0)'
_cell_angle_alpha                90.00
_cell_angle_beta                 99.092(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7117(4)
_cell_length_b                   7.4436(2)
_cell_length_c                   13.4290(5)
_cell_measurement_reflns_used    4268
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      67.11
_cell_measurement_theta_min      4.18
_cell_volume                     1057.29(6)
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7399
_diffrn_reflns_theta_full        67.11
_diffrn_reflns_theta_max         67.11
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    1.715
_exptl_absorpt_correction_T_max  0.842
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       0.0051(6)
_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   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0148P)^2^+0.1540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                2371
_reflns_number_total             2529
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400873c_si_001.cif
_cod_data_source_block           13
_cod_original_sg_symbol_Hall     P2yb
_cod_database_code               4028424