Sequential C-H Functionalization Reactions for the Enantioselective Synthesis of Highly Functionalized 2,3-Dihydrobenzofurans
Hengbin Wang; Gang Li; Keary M. Engle; Jin-Quan Yu; Huw M. L. Davies; Journal of the American Chemical Society 135 (2013) 6774–6777; doi:10.1021/ja401731d

data_4119728
_publ_contact_author_name
;
;
_publ_section_title
;
 Sequential C-H Functionalization Reactions for the Enantioselective
 Synthesis of Highly Functionalized 2,3-Dihydrobenzofurans
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6774
_journal_page_last               6777
_journal_paper_doi               10.1021/ja401731d
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 O6, H2 O'
_chemical_formula_sum            'C18 H20 O7'
_chemical_formula_weight         348.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-15
_audit_creation_method
; 
  Olex2 1.2-alpha 
  (compiled Jan 11 2012 18:49:03, GUI svn.r4030) 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.1880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2635(3)
_cell_length_b                   5.08800(10)
_cell_length_c                   15.9439(4)
_cell_measurement_reflns_used    5427
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.60
_cell_measurement_theta_min      2.79
_cell_volume                     826.06(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_publication_material
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_structure_refinement
; 
XL, G.M. Sheldrick, Acta Cryst. 
(2008). A64, 112-122 
;
_computing_structure_solution
; 
XM, G.M. Sheldrick, Acta Cryst. 
(2008). A64, 112-122 
;
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6103
_diffrn_reflns_theta_full        68.79
_diffrn_reflns_theta_max         68.79
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
R(int) was 0.0365 before and 0.0186 after correction. 
The Ratio of minimum to maximum transmission is 0.9485. 
The \l/2 correction factor is Not present. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.311
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0707P)^2^+0.1073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                2276
_reflns_number_total             2285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja401731d_si_002.cif
_cod_data_source_block           hwxii014
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4119728