A General Organocatalytic Approach toward the Enantioselective Total Synthesis of Indolizidine Based Alkaloids.
Abels, Falko; Lindemann, Chris; Koch, Eva; Schneider, Christoph; Organic letters 14 (2012) 5972–5975; doi:10.1021/ol302871u

data_1508774
_publ_section_title
;
 A General Organocatalytic Approach toward the Enantioselective Total
 Synthesis of Indolizidine Based Alkaloids.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5972
_journal_page_last               5975
_journal_paper_doi               10.1021/ol302871u
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H23 N O4'
_chemical_formula_weight         317.37
_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   difmap
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_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.99280(10)
_cell_length_b                   12.5308(3)
_cell_length_c                   22.4250(4)
_cell_measurement_reflns_used    7484
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      67.1156
_cell_measurement_theta_min      3.5242
_cell_volume                     1684.00(6)
_computing_cell_refinement
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'ORTEP3 for WINDOWS (L.J.Ferrugia)'
_computing_publication_material  'WINGX (L.J. Ferrugia)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.356
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0376748
_diffrn_orient_matrix_UB_12      0.0253965
_diffrn_orient_matrix_UB_13      0.0664625
_diffrn_orient_matrix_UB_21      0.1189852
_diffrn_orient_matrix_UB_22      -0.1044297
_diffrn_orient_matrix_UB_23      0.0172594
_diffrn_orient_matrix_UB_31      0.2248911
_diffrn_orient_matrix_UB_32      0.0595724
_diffrn_orient_matrix_UB_33      0.0020515
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16144
_diffrn_reflns_theta_full        67.23
_diffrn_reflns_theta_max         67.23
_diffrn_reflns_theta_min         3.94
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.35214
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_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.1385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                2913
_reflns_number_total             3006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302871u_si_002.cif
_cod_data_source_block           x1602
_cod_database_code               1508774