Highly Enantioselective Simmons-Smith Fluorocyclopropanation of Allylic Alcohols via the Halogen Scrambling Strategy of Zinc Carbenoids
Louis-Philippe B. Beaulieu; Jakob F. Schneider; André B. Charette; Journal of the American Chemical Society 135 (2013) 7819–7822; doi:10.1021/ja402393w

data_4119813
_publ_section_title
;
 Highly Enantioselective Simmons-Smith Fluorocyclopropanation of Allylic
 Alcohols via the Halogen Scrambling Strategy of Zinc Carbenoids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7819
_journal_page_last               7822
_journal_paper_doi               10.1021/ja402393w
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C17 H12 Cl F N2 O6'
_chemical_formula_sum            'C17 H12 Cl F N2 O6'
_chemical_formula_weight         394.74
_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                 100.755(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7405(8)
_cell_length_b                   6.7959(4)
_cell_length_c                   17.2665(9)
_cell_measurement_reflns_used    10026
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.33
_cell_measurement_theta_min      2.61
_cell_volume                     1699.29(16)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL  (Bruker AXS, 2003)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32925
_diffrn_reflns_theta_full        70.72
_diffrn_reflns_theta_max         70.72
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    2.458
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_correction_T_min  0.7806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       Needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
'Flack, H.D. and Schwarzenbach, D. (1999), 2818 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.007(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6364
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0549
_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^)+(0.1289P)^2^+0.0136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                5855
_reflns_number_total             6364
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja402393w_si_001.cif
_cod_data_source_block           cha224
_cod_database_code               4119813