Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations
Dorine Belmessieri; Louis C. Morrill; Carmen Simal; Alexandra M. Z. Slawin; Andrew D. Smith; Journal of the American Chemical Society 133 (2011) 2714–2720; doi:10.1021/ja109975c

data_4105688
_publ_section_title
;
 Organocatalytic Functionalization of Carboxylic Acids:
 Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael
 Addition-Lactonizations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2714
_journal_page_last               2720
_journal_paper_doi               10.1021/ja109975c
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H15 Br O4'
_chemical_formula_sum            'C19 H15 Br O4'
_chemical_formula_weight         387.22
_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            8
_cell_length_a                   6.3142(11)
_cell_length_b                   19.786(3)
_cell_length_c                   26.184(4)
_cell_measurement_reflns_used    11122
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.6
_cell_volume                     3271.2(9)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20897
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0696
_reflns_number_gt                5056
_reflns_number_total             5964
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja109975c_si_005.cif
_cod_data_source_block           10
_cod_database_code               4105688