Au-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Isocyanoacetates with Maleimides
Silvia Padilla; Javier Adrio; Juan C. Carretero; Journal of Organic Chemistry 77 (2012) 4161–4166; doi:10.1021/jo3003425

data_4027159
_publ_section_title
;
 Au-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Isocyanoacetates
 with Maleimides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4161
_journal_page_last               4166
_journal_paper_doi               10.1021/jo3003425
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42
_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                   8.992(9)
_cell_length_b                   12.614(12)
_cell_length_c                   17.079(16)
_cell_measurement_temperature    293(2)
_cell_volume                     1937(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    0.1564
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1543
_diffrn_reflns_theta_full        18.97
_diffrn_reflns_theta_max         18.97
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             808
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         1543
_refine_ls_number_restraints     170
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0822
_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^)+(0.1306P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1950
_refine_ls_wR_factor_ref         0.2338
_reflns_number_gt                984
_reflns_number_total             1543
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo3003425_si_003.cif
_cod_data_source_block           jd03spd1n
_cod_database_code               4027159