Asymmetric Morita-Baylis-Hillman reaction catalyzed by isophoronediamine-derived bis(thio)urea organocatalysts.
Berkessel, Albrecht; Roland, Katrin; Neudörfl, Jörg M; Organic letters 8 (2006) 4195–4198; doi:10.1021/ol061298m

data_1506122
_publ_section_title
;
 Asymmetric Morita-Baylis-Hillman reaction catalyzed by
 isophoronediamine-derived bis(thio)urea organocatalysts.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4195
_journal_page_last               4198
_journal_paper_doi               10.1021/ol061298m
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C24 H32 N4 S2'
_chemical_formula_sum            'C24 H32 N4 S2'
_chemical_formula_weight         440.66
_chemical_name_systematic
; 
N-Phenyl-N'-[(1R,3S)-3-[[[(phenylamino)thioxomethyl]amino]
methyl]-3,5,5-trimethylcyclohexyl]thiourea
;
_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                   7.5688(3)
_cell_length_b                   9.5287(4)
_cell_length_c                   33.9726(14)
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      1.20
_cell_volume                     2450.13(17)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.1007
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            9844
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.20
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                3529
_reflns_number_total             5183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061298msi20060605_121914.cif
_cod_data_source_block           1c
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1506122