Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes.
Cinar, M. Emin; Engelen, Bernward; Panthöfer, Martin; Deiseroth, Hans-Jörg; Schlirf, Jens; Schmittel, Michael; Beilstein journal of organic chemistry 12 (2016) 813–824; doi:10.3762/bjoc.12.80

data_4031973
_publ_section_title
;
 Scope and mechanism of the highly stereoselective metal-mediated domino
 aldol reactions of enolates with aldehydes.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              813
_journal_page_last               824
_journal_paper_doi               10.3762/bjoc.12.80
_journal_volume                  12
_journal_year                    2016
_chemical_formula_sum            'C25 H26 O3'
_chemical_formula_weight         374.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_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                   8.6709(9)
_cell_length_b                   12.9435(16)
_cell_length_c                   17.587(2)
_cell_measurement_temperature    120(2)
_cell_volume                     1973.8(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23717
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_correction_T_min  0.9378
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.201
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+1.0291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                2918
_reflns_number_total             3268
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-12-80-S2.cif
_cod_data_source_block           racem
_cod_depositor_comments
'Adding full bibliography for 4031973--4031974.cif.'
_cod_database_code               4031973