Enantioselective vinylogous Mukaiyama aldol reaction of α-ketoesters under bifunctional organocatalysis.
Del Río-Rodríguez, Roberto; Laina-Martín, Víctor; Fernández-Salas, Jose A; Alemán, José; Chemical communications (Cambridge, England) 57 (2021) 11665–11668; doi:10.1039/d1cc04263g

data_7129105
_publ_section_title
;
 Enantioselective vinylogous Mukaiyama aldol reaction of \a-ketoesters
 under bifunctional organocatalysis.
;
_journal_issue                   88
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11665
_journal_page_last               11668
_journal_paper_doi               10.1039/d1cc04263g
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H13 Br O3'
_chemical_formula_weight         285.13
_chemical_name_common            RR-626-F1_200K
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc28jcsz
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.8320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3815(2)
_cell_length_b                   7.13240(10)
_cell_length_c                   10.0251(2)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      26.1462
_cell_measurement_theta_min      2.5026
_cell_volume                     581.92(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22324
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.09
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.521
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.295
_refine_ls_abs_structure_details
;

Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0183
_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^)+(0.0223P)^2^+0.1857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                2051
_reflns_number_total             2111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04263g2.cif
_cod_data_source_block           03363
_cod_depositor_comments          'Adding full bibliography for 7129105.cif.'
_cod_database_code               7129105
_shelx_res_checksum              82183