Highly Enantioselective Intramolecular Copper Catalyzed C-H Insertion Reactions of α-Diazosulfones
Christopher J. Flynn; Curtis J. Elcoate; Simon E. Lawrence; Anita R. Maguire; Journal of the American Chemical Society 132 (2010) 1184–1185; doi:10.1021/ja909713a

data_4101843
_publ_contact_author_address
;Department of Chemistry & School of Pharmacy
Analytical and Biological Chemistry Research Facility
University College Cork
Cork
Ireland
;
_publ_contact_author_email       a.maguire@ucc.ie
_publ_contact_author_fax         +353(21)4901770
_publ_contact_author_name        'Anita R. Maguire'
_publ_contact_author_phone       +353(21)4901693
_publ_section_title
;
 Highly Enantioselective Intramolecular Copper Catalyzed C-H Insertion
 Reactions of \a-Diazosulfones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1184
_journal_page_last               1185
_journal_paper_doi               10.1021/ja909713a
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H16 O4 S'
_chemical_formula_sum            'C13 H16 O4 S'
_chemical_formula_weight         268.32
_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           'APEX2 v2009.3-0'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7607(7)
_cell_length_b                   11.1384(16)
_cell_length_c                   20.346(3)
_cell_measurement_reflns_used    1044
_cell_measurement_temperature    293.(2)
_cell_measurement_theta_max      23.3048
_cell_measurement_theta_min      2.7116
_cell_volume                     1305.5(3)
_computing_cell_refinement       'SAINT V7.60A (Bruker AXS, 2008)'
_computing_data_collection       'Bruker Instrument Service v2009, 3, 0, 0'
_computing_data_reduction        'SAINT V7.60A (Bruker AXS, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL-97; Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       '\f & \w  scans'
_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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6951
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_correction_T_min  0.6370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs Version 2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prismatice needle'
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.251
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0473P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                1991
_reflns_number_total             2811
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja909713a_si_001_2.cif
_cod_data_source_block           Compound_9
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4101843