Copper-Catalyzed Diastereo- and Enantioselective Desymmetrization of Cyclopropenes: Synthesis of Cyclopropylboronates.
Parra, Alejandro; Amenós, Laura; Guisán-Ceinos, Manuel; López, Aurora; García Ruano, José Luis; Tortosa, Mariola; Journal of the American Chemical Society  (2014) 141031133923007–; doi:10.1021/ja510419z

data_4122882
_publ_section_title
;
 Copper-Catalyzed Diastereo- and Enantioselective Desymmetrization of
 Cyclopropenes: Synthesis of Cyclopropylboronates.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141031133923007
_journal_paper_doi               10.1021/ja510419z
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H14 Cl N O4'
_chemical_formula_weight         331.74
_chemical_name_common            MGC-109
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1340(2)
_cell_length_b                   10.6384(3)
_cell_length_c                   21.0677(7)
_cell_measurement_reflns_used    8781
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      24.3962
_cell_measurement_theta_min      2.7212
_cell_volume                     1598.92(8)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24711
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.237
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+0.2539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                2399
_reflns_number_total             2935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja510419z_si_003.cif
_cod_data_source_block           I
_cod_database_code               4122882