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_4031974
_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            'C19 H26 O3'
_chemical_formula_weight         302.40
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.032(2)
_cell_length_b                   18.500(4)
_cell_length_c                   9.118(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1595.5(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.1040
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12534
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0019(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+0.0063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                2485
_reflns_number_total             3783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-12-80-S3.cif
_cod_data_source_block           n2
_cod_depositor_comments
'Adding full bibliography for 4031973--4031974.cif.'
_cod_original_cell_volume        1595.5(6)
_cod_database_code               4031974