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_7152433
_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_formula_moiety         'C17 H14 Cl N O4'
_chemical_formula_sum            'C17 H14 Cl N O4'
_chemical_formula_weight         331.74
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.646(3)
_cell_angle_beta                 80.311(3)
_cell_angle_gamma                70.794(3)
_cell_formula_units_Z            4
_cell_length_a                   8.7119(13)
_cell_length_b                   12.7240(18)
_cell_length_c                   15.850(2)
_cell_measurement_reflns_used    7808
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      33.53
_cell_measurement_theta_min      2.48
_cell_volume                     1521.8(4)
_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    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.878
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25995
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         34.20
_diffrn_reflns_theta_min         1.82
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9328
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         11075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.5379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                7614
_reflns_number_total             11075
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25813g.txt
_cod_data_source_block           1097GuillotICMMO
_cod_database_code               7152433