Very high stereoselectivity in organocatalyzed desymmetrizing aldol reactions of 3-substituted cyclobutanones.
Aitken, David J.; Bernard, Angela M.; Capitta, Francesca; Frongia, Angelo; Guillot, Régis; Ollivier, Jean; Piras, Pier Paolo; Secci, Francesco; Spiga, Marco; Organic & biomolecular chemistry 10 (2012) 5045–5048; doi:10.1039/c2ob25813g

data_7152432
_publ_section_title
;
 Very high stereoselectivity in organocatalyzed desymmetrizing aldol
 reactions of 3-substituted cyclobutanones.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5045
_journal_page_last               5048
_journal_paper_doi               10.1039/c2ob25813g
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H14 Cl N O5'
_chemical_formula_sum            'C17 H14 Cl N O5'
_chemical_formula_weight         347.74
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 101.569(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2365(4)
_cell_length_b                   9.7935(4)
_cell_length_c                   17.7681(8)
_cell_measurement_reflns_used    3312
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      21.00
_cell_measurement_theta_min      2.34
_cell_volume                     1574.61(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXLS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 120
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_sigmaI/netI    0.0987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37446
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         1.17
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kapa X8 APEX II Bruker ICMMO FRANCE'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         9323
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1446
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+1.5996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1606
_reflns_number_gt                5216
_reflns_number_total             9323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25813g.txt
_cod_data_source_block           922GuillotICMMO
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7152432