Remote Asymmetric Bromination Reaction with Vinylketene Silyl N,O-Acetal and Its Application to Total Synthesis of Pellasoren A.
Sekiya, Shinji; Okumura, Mao; Kubota, Kei; Nakamura, Tatsuya; Sekine, Daisuke; Hosokawa, Seijiro; Organic letters 19 (2017) 2394–2397; doi:10.1021/acs.orglett.7b00920

data_1545781
_publ_section_title
;
 Remote Asymmetric Bromination Reaction with Vinylketene Silyl N,O-Acetal
 and Its Application to Total Synthesis of Pellasoren A.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2394
_journal_page_last               2397
_journal_paper_doi               10.1021/acs.orglett.7b00920
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C14 H21 N O4 S'
_chemical_formula_sum            'C14 H21 N O4 S'
_chemical_formula_weight         299.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.03(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.811(6)
_cell_length_b                   5.342(2)
_cell_length_c                   19.823(7)
_cell_measurement_reflns_used    4189
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      3.21
_cell_volume                     1549.0(10)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7392
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.205
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.59
_refine_ls_abs_structure_details
;
 Flack x determined using 540 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0866
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1020P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2479
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                1814
_reflns_number_total             3462
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol7b00920_si_002.cif
_cod_data_source_block           test20170213
_cod_depositor_comments
'Adding full bibliography for 1545781--1545782.cif.'
_cod_database_code               1545781
_shelxl_version_number           2014/6
_shelx_res_checksum              42822
_shelx_hkl_checksum              72895