Asymmetric Histidine-Catalyzed Cross-Aldol Reactions of Enolizable Aldehydes: Access to Defined Configured Quaternary Stereogenic Centers
Morris Markert; Ulf Scheffler; Rainer Mahrwald; Journal of the American Chemical Society 131 (2009) 16642–16643; doi:10.1021/ja907054y

data_4105370
_publ_section_title
;
 Asymmetric Histidine-Catalyzed Cross-Aldol Reactions of Enolizable
 Aldehydes: Access to Defined Configured Quaternary Stereogenic Centers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16642
_journal_page_last               16643
_journal_paper_doi               10.1021/ja907054y
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C10 H18 O4'
_chemical_formula_sum            'C10 H18 O4'
_chemical_formula_weight         202.24
_chemical_name_systematic
; 
 (R)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-
dimethylpropanal 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.146(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0434(9)
_cell_length_b                   8.5691(10)
_cell_length_c                   10.8387(15)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      5
_cell_volume                     559.04(13)
_computing_cell_refinement       'IPDS2.87 (Stoe & Cie, 1997)'
_computing_data_collection       'IPDS2.87 (Stoe & Cie, 1997)'
_computing_data_reduction        'IPDS2.87 (Stoe & Cie, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 6.667
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'Stoe IPDS diffractometer'
_diffrn_measurement_method       '\f-oscill.,\f-incr.=1.3\%,168 exposures'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3941
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0427P)^2^+0.0701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                2064
_reflns_number_total             2130
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ja907054y_si_003.cif
_cod_data_source_block           3g
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4105370