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_1508773
_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            'C17 H21 N O4'
_chemical_formula_weight         303.35
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_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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_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.78493(7)
_cell_length_b                   12.86729(13)
_cell_length_c                   21.7765(2)
_cell_measurement_reflns_used    12158
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      67.1286
_cell_measurement_theta_min      3.432
_cell_volume                     1620.96(3)
_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)
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_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    'ORTEP for WINDOWS (L.J.Ferrugia)'
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_diffrn_ambient_temperature      130(2)
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
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_diffrn_orient_matrix_UB_11      -0.0893576
_diffrn_orient_matrix_UB_12      -0.002799
_diffrn_orient_matrix_UB_13      0.0666344
_diffrn_orient_matrix_UB_21      0.0098502
_diffrn_orient_matrix_UB_22      0.1194973
_diffrn_orient_matrix_UB_23      0.0027012
_diffrn_orient_matrix_UB_31      -0.2507643
_diffrn_orient_matrix_UB_32      0.0057682
_diffrn_orient_matrix_UB_33      -0.0236415
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23464
_diffrn_reflns_theta_full        67.24
_diffrn_reflns_theta_max         67.24
_diffrn_reflns_theta_min         3.99
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  0.8688
_exptl_absorpt_correction_T_min  0.6708
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        CrysAlisPro, Agilent Technologies,
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        (compiled Jan 23 2012,18:06:46)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0020(4)
_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   1.012
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.084
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.5271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.094
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                2858
_reflns_number_total             2879
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302871u_si_002.cif
_cod_data_source_block           x1600
_cod_original_sg_symbol_H-M      'P 2(1) 2(1) 2(1)'
_cod_database_code               1508773