Gold meets rhodium: tandem one-pot synthesis of β-disubstituted ketones via Meyer-Schuster rearrangement and asymmetric 1,4-addition.
Hansmann, Max M.; Hashmi, A Stephen K; Lautens, Mark; Organic letters 15 (2013) 3226–3229; doi:10.1021/ol4011739

data_1556173
_publ_section_title
;
 Gold meets rhodium: tandem one-pot synthesis of \b-disubstituted ketones
 via Meyer-Schuster rearrangement and asymmetric 1,4-addition.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3226
_journal_page_last               3229
_journal_paper_doi               10.1021/ol4011739
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H21 Br O'
_chemical_formula_sum            'C23 H21 Br O'
_chemical_formula_weight         393.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0001(3)
_cell_length_b                   10.0316(4)
_cell_length_c                   19.1693(6)
_cell_measurement_reflns_used    2009
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      55.16
_cell_measurement_theta_min      4.61
_cell_volume                     1923.01(11)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      230(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21233
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         4.613
_diffrn_source                   'Bruker ImuS'
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_T_max  0.7428
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 969 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.029(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         10053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0668P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                8007
_reflns_number_total             10053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol4011739_si_002.cif
_cod_data_source_block           twin
_cod_database_code               1556173
_shelx_estimated_absorpt_t_min   0.891
_shelx_estimated_absorpt_t_max   0.917
_shelxl_version_number           2013-2