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_4122880
_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            'C21 H32 B N O2'
_chemical_formula_weight         341.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 100.364(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1015(5)
_cell_length_b                   13.0117(6)
_cell_length_c                   15.9790(8)
_cell_measurement_temperature    296(2)
_cell_volume                     2065.98(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12553
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.03
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9858
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.0907
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1693P)^2^+1.1050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2581
_refine_ls_wR_factor_ref         0.3097
_reflns_number_gt                1975
_reflns_number_total             3607
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja510419z_si_002.cif
_cod_data_source_block           datos_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4122880