Chiral Phosphine-Silver(I) Complex Catalyzed Enantioselective Interrupted Feist-Bénary Reaction with Ynones: The Aldol-Cycloisomerization Cascade.
Sinha, Debarshi; Biswas, Arnab; Singh, Vinod K.; Organic letters 17 (2015) 3302–3305; doi:10.1021/acs.orglett.5b01468

data_1520657
_publ_section_title
;
 Chiral Phosphine-Silver(I) Complex Catalyzed Enantioselective Interrupted
 Feist-B\'enary Reaction with Ynones: The Aldol-Cycloisomerization
 Cascade.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3302
_journal_page_last               3305
_journal_paper_doi               10.1021/acs.orglett.5b01468
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H17 Br O5'
_chemical_formula_weight         393.23
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.294(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6762(6)
_cell_length_b                   10.5443(11)
_cell_length_c                   14.1611(14)
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.98
_cell_measurement_theta_min      2.42
_cell_volume                     833.92(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1484
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14514
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.891
_diffrn_reflns_theta_min         2.422
_exptl_absorpt_coefficient_mu    2.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.780
_exptl_transmission_factor_min   0.556
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         14514
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                11178
_reflns_number_total             14514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01468_si_002.cif
_cod_data_source_block           ds171
_cod_depositor_comments          'Adding full bibliography for 1520657.cif.'
_cod_database_code               1520657
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.522
_shelx_estimated_absorpt_t_max   0.789
_shelx_res_checksum              87916
_shelx_hkl_checksum              12648