Development of the Enantioselective Addition of Ethyl Diazoacetate to Aldehydes: Asymmetric Synthesis of 1,2-Diols
Barry M. Trost; Sushant Malhotra; Philipp Koschker; Pascal Ellerbrock; Journal of the American Chemical Society 134 (2012) 2075–2084; doi:10.1021/ja206995s

data_4117360
_publ_contact_author_address     'Dept. of Chemistry, Stanford University'
_publ_contact_author_email       sushantm@stanford.edu
_publ_contact_author_name        'Sushant Malhotra'
_publ_contact_author_phone       '+1 317 490 3615'
_publ_section_title
;
 Development of the Enantioselective Addition of Ethyl Diazoacetate to
 Aldehydes: Asymmetric Synthesis of 1,2-Diols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2075
_journal_page_last               2084
_journal_paper_doi               10.1021/ja206995s
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H25 Br O6'
_chemical_formula_sum            'C24 H25 Br O6'
_chemical_formula_weight         489.35
_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                90.00
_cell_angle_beta                 93.991(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8101(6)
_cell_length_b                   13.0126(10)
_cell_length_c                   12.8280(10)
_cell_measurement_reflns_used    2563
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.35
_cell_measurement_theta_min      2.23
_cell_volume                     1134.02(16)
_computing_cell_refinement       'Bruker SAINT v7.68A'
_computing_data_collection       'Bruker APEX-II v2010-3'
_computing_data_reduction        'Bruker SAINT v7.68A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of \w and \f-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  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0803
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12969
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    1.849
_exptl_absorpt_correction_T_max  0.7950
_exptl_absorpt_correction_T_min  0.6161
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       blade
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2232 Friedel pairs measured'
_refine_ls_abs_structure_Flack   0.000(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4446
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                3643
_reflns_number_total             4446
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja206995s_si_004.cif
_cod_data_source_block           su032
_cod_database_code               4117360