Stereoselective and Regiodivergent Allylic Suzuki-Miyaura Cross-Coupling of 2-Ethoxydihydropyranyl Boronates: Synthesis and Confirmation of Absolute Stereochemistry of Diospongin B.
Rybak, Taras; Hall, Dennis G.; Organic letters 17 (2015) 4156–4159; doi:10.1021/acs.orglett.5b01906

data_1529421
_publ_section_title
;
 Stereoselective and Regiodivergent Allylic Suzuki-Miyaura Cross-Coupling
 of 2-Ethoxydihydropyranyl Boronates: Synthesis and Confirmation of
 Absolute Stereochemistry of Diospongin B.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4156
_journal_page_last               4159
_journal_paper_doi               10.1021/acs.orglett.5b01906
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H18 O4'
_chemical_formula_sum            'C13 H18 O4'
_chemical_formula_weight         238.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.240(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9170(15)
_cell_length_b                   7.864(2)
_cell_length_c                   13.651(3)
_cell_measurement_reflns_used    4050
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      3.00
_cell_volume                     623.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5557
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         1.521
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9184
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       fragment
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 885 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.8(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.0642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2363
_reflns_number_total             2822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01906_si_003.cif
_cod_data_source_block           dgh1501
_cod_depositor_comments
'Adding full bibliography for 1529421--1529422.cif.'
_cod_database_code               1529421
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              76763
_shelx_hkl_checksum              92579