Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation
Marcus Angelin; Martin Rahm; Andreas Fischer; Tore Brinck; Olof Ramström; Journal of Organic Chemistry 75 (2010) 5882–5887; doi:10.1021/jo100868z

data_4025614
_publ_contact_author_address
;
Organic Chemistry
School of Chemical Science and Engineering
Royal Institute of Technology (KTH)
100 44 Stockholm
Sweden
;
_publ_contact_author_email       ramstrom@kth.se
_publ_contact_author_name        'Olof Ramstr\"om'
_publ_contact_author_phone       '+46(0)8 790-6915'
_publ_section_title
;
 Diastereoselective One-Pot Tandem Synthesis of 3-Substituted
 Isoindolinones: A Mechanistic Investigation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5882
_journal_page_last               5887
_journal_paper_doi               10.1021/jo100868z
_journal_volume                  75
_journal_year                    2010
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C10 H10 N2 O4'
_chemical_formula_sum            'C10 H10 N2 O4'
_chemical_formula_weight         222.2
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2010-01-25 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.11(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.626(2)
_cell_length_b                   5.8228(12)
_cell_length_c                   16.673(4)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    299
_cell_measurement_theta_max      20.7
_cell_measurement_theta_min      4.0
_cell_volume                     1000.5(4)
_computing_cell_refinement       Dirax
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      299
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.129
_diffrn_reflns_av_sigmaI/netI    0.097
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10068
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         4.7
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.142
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0439P)^2^+0.1631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.116
_reflns_number_gt                982
_reflns_number_total             1846
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo100868z_si_004.cif
_cod_data_source_block           ramstroem090624
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025614