Asymmetric Rh(II)-Catalyzed Cyclopropanation of Alkenes with Diacceptor Diazo Compounds: p-Methoxyphenyl Ketone as a General Stereoselectivity Controlling Group
Vincent N. G. Lindsay; Cyril Nicolas; André B. Charette; Journal of the American Chemical Society 133 (2011) 8972–8981; doi:10.1021/ja201237j

data_4106232
_publ_section_title
;
 Asymmetric Rh(II)-Catalyzed Cyclopropanation of Alkenes with Diacceptor
 Diazo Compounds: p-Methoxyphenyl Ketone as a General Stereoselectivity
 Controlling Group
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8972
_journal_page_last               8981
_journal_paper_doi               10.1021/ja201237j
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C19 H18 O4'
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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
_cell_angle_beta                 91.981(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9911(1)
_cell_length_b                   5.5915(1)
_cell_length_c                   17.4447(3)
_cell_measurement_reflns_used    7182
_cell_measurement_temperature    150
_cell_measurement_theta_max      71.87
_cell_measurement_theta_min      2.53
_cell_volume                     779.00(2)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, )'
_computing_data_collection       'APEX2  (Bruker AXS, 1)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, )'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10190
_diffrn_reflns_theta_full        72.73
_diffrn_reflns_theta_max         72.73
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.8490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), 1134 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_extinction_coef       0.036(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0605P)^2^+0.0476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                2740
_reflns_number_total             2839
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja201237j_si_003.cif
_cod_data_source_block           cha200
_cod_database_code               4106232