Sequential Mukaiyama-Michael reaction induced by carbon acids.
Yanai, Hikaru; Kobayashi, Osamu; Takada, Kenji; Isono, Takuya; Satoh, Toshifumi; Matsumoto, Takashi; Chemical communications (Cambridge, England) 52 (2016) 3280–3283; doi:10.1039/c5cc10115h

data_7118372
_publ_section_title
;
 Sequential Mukaiyama-Michael reaction induced by carbon acids.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3280
_journal_page_last               3283
_journal_paper_doi               10.1039/c5cc10115h
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 Br O5'
_chemical_formula_sum            'C18 H19 Br O5'
_chemical_formula_weight         395.24
_chemical_melting_point          94.0
_chemical_name_systematic
;
Ethyl 2-((3S*,4S*)-6-bromo-2-oxo-3-((R*)-3-oxocyclopentyl)chroman-4-yl)acetate
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'April 22 2015'
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-03 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.091(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   11.3068(19)
_cell_length_b                   9.6829(16)
_cell_length_c                   24.116(4)
_cell_measurement_reflns_used    3963
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      3.05
_cell_volume                     2571.7(7)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12184
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    2.422
_exptl_absorpt_correction_T_max  0.8683
_exptl_absorpt_correction_T_min  0.7127
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         6361
_refine_ls_number_restraints     452
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0290
_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          0.0568
_refine_ls_wR_factor_ref         0.0589
_reflns_number_gt                5637
_reflns_number_total             6361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc10115h2.cif
_cod_data_source_block           syn-14b
_cod_depositor_comments
'Adding full bibliography for 7118367--7118375.cif.'
_cod_original_sg_symbol_H-M      'P c     '
_cod_database_code               7118372