Asymmetric Organocatalytic Direct Aldol Reactions of Ketones with α-Keto Acids and Their Application to the Synthesis of 2-Hydroxy-γ-butyrolactones
Xiao-Ying Xu; Zhuo Tang; Yan-Zhao Wang; Shi-Wei Luo; Lin-Feng Cun; Liu-Zhu Gong; Journal of Organic Chemistry 72 (2007) 9905–9913; doi:10.1021/jo701868t

data_4023110
_publ_section_title
;
 Asymmetric Organocatalytic Direct Aldol Reactions of Ketones with
 \a-Keto Acids and Their Application to the Synthesis of
 2-Hydroxy-\g-butyrolactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9905
_journal_page_last               9913
_journal_paper_doi               10.1021/jo701868t
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C12 H13 N O5'
_chemical_formula_weight         251.23
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 92.560(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.630(3)
_cell_length_b                   6.028(3)
_cell_length_c                   17.632(10)
_cell_measurement_temperature    293(2)
_cell_volume                     597.7(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3807
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.110
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.520
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1929
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.520
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0379
_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^)+(0.1070P)^2^+1.0375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                1754
_reflns_number_total             1929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701868t-File002.cif
_cod_data_source_block           sad
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023110