Asymmetric Synthesis of 2-Alkyl-Substituted 2,5-Dihydropyrroles from Optically Active Aza-Baylis-Hillman Adducts. Formal Synthesis of (-)-Trachelanthamidine.
Shingo Ishikawa; Fumiaki Noguchi; Akio Kamimura; Journal of Organic Chemistry 75 (2010) 3578–3586; doi:10.1021/jo100315j

data_4025442
_publ_section_title
;
 Asymmetric Synthesis of 2-Alkyl-Substituted 2,5-Dihydropyrroles from
 Optically Active Aza-Baylis-Hillman Adducts. Formal Synthesis of
 (-)-Trachelanthamidine.
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3578
_journal_page_last               3586
_journal_paper_doi               10.1021/jo100315j
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C25 H39 N O5 S Si '
_chemical_formula_sum            'C25 H39 N O5 S Si'
_chemical_formula_weight         493.73
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.144(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.8985(10)
_cell_length_b                   10.8903(8)
_cell_length_c                   11.9769(8)
_cell_measurement_reflns_used    8510
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      3.5
_cell_volume                     1457.01(19)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3462
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             532.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.478
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     342
_refine_ls_number_reflns         2181
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/\s^2^(Fo)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0381
_reflns_number_gt                2163
_reflns_number_total             3462
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo100315j_si_002.cif
_cod_data_source_block           '_SI07015'
_cod_original_cell_volume        1457.00(18)
_cod_original_formula_sum        'C25 H39 N O5 S Si '
_cod_database_code               4025442