One-pot organocatalytic enantioselective domino double-Michael reaction and pictet-spengler-lactamization reaction. A facile entry to the "inside yohimbane" system with five contiguous stereogenic centers.
Hong, Bor-Cherng; Liao, Wei-Kai; Dange, Nitin S.; Liao, Ju-Hsiou; Organic letters 15 (2013) 468–471; doi:10.1021/ol3032329

data_1508865
_publ_section_title
;
 One-pot organocatalytic enantioselective domino double-Michael reaction
 and pictet-spengler-lactamization reaction. A facile entry to the
 &quot;inside yohimbane&quot; system with five contiguous stereogenic
 centers.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              468
_journal_page_last               471
_journal_paper_doi               10.1021/ol3032329
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_sum            'C25 H24 Cl N3 O3'
_chemical_formula_weight         449.92
_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   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            4
_cell_length_a                   8.1146(8)
_cell_length_b                   9.2164(9)
_cell_length_c                   35.493(4)
_cell_measurement_reflns_used    997
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.529
_cell_measurement_theta_min      -23.529
_cell_volume                     2654.4(5)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'Wingx publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'phi-omega scan'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6427
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.15
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9567
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0788P)^2^+0.4704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                5285
_reflns_number_total             6427
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3032329_si_003.cif
_cod_data_source_block           lwk002-sr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               1508865