Organocatalyzed Asymmetric Aldol Reactions of Ketones and β,γ-Unsaturated α-Ketoesters and Phenylglyoxal Hydrates.
Konda, Swapna; Guo, Qun-Sheng; Abe, Manabu; Huang, Huicai; Arman, Hadi; Zhao, John C.-G.; The Journal of organic chemistry 80 (2015) 806–815; doi:10.1021/jo502254e

data_4030389
_publ_section_title
;
 Organocatalyzed Asymmetric Aldol Reactions of Ketones and
 \b,\g-Unsaturated \a-Ketoesters and Phenylglyoxal Hydrates.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              806
_journal_page_last               815
_journal_paper_doi               10.1021/jo502254e
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H15 Br O3'
_chemical_formula_sum            'C14 H15 Br O3'
_chemical_formula_weight         311.17
_chemical_name_systematic
; 
(R)-2[(S)-2-(4-bromophneyl)-1-hydroxy-2-oxoethyl]cyclohexanone 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.422(2)
_cell_length_b                   10.122(3)
_cell_length_c                   16.852(5)
_cell_measurement_reflns_used    7689
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.3
_cell_volume                     1266.0(6)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1235
_diffrn_reflns_av_sigmaI/netI    0.1050
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4580
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.244
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.247
_refine_diff_density_min         -1.500
_refine_diff_density_rms         0.153
_refine_ls_abs_structure_details 'Flack(1983),1182 Friedel pairs'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0470P)^2^+3.7000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                2691
_reflns_number_total             2857
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502254e_si_003.cif
_cod_data_source_block           BHOC
_cod_depositor_comments
'Adding full bibliography for 4030388--4030389.cif.'
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4030389