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_1545782
_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         'C12 H18 Br N O3'
_chemical_formula_sum            'C12 H18 Br N O3'
_chemical_formula_weight         304.18
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.336(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.0060(10)
_cell_length_b                   6.2513(6)
_cell_length_c                   10.8417(12)
_cell_measurement_reflns_used    4493
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.77
_cell_volume                     677.00(12)
_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  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      173
_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  0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6640
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        27.440
_diffrn_reflns_theta_max         27.440
_diffrn_reflns_theta_min         3.764
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.042
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.88
_refine_diff_density_min         -1.04
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1073 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0842P)^2^+0.2192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1814
_reflns_number_gt                1841
_reflns_number_total             2757
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol7b00920_si_001.cif
_cod_data_source_block           mao-Br
_cod_depositor_comments
'Adding full bibliography for 1545781--1545782.cif.'
_cod_original_cell_volume        677.01(12)
_cod_database_code               1545782