Stereoselective titanium-mediated aldol reactions of a chiral lactate-derived ethyl ketone with ketones.
Alcoberro, Sandra; Gómez-Palomino, Alejandro; Solà, Ricard; Romea, Pedro; Urpí, Fèlix; Font-Bardia, Mercè; Organic letters 16 (2014) 584–587; doi:10.1021/ol403461b

data_1513394
_publ_section_title
;
 Stereoselective titanium-mediated aldol reactions of a chiral
 lactate-derived ethyl ketone with ketones.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              584
_journal_page_last               587
_journal_paper_doi               10.1021/ol403461b
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C8 H12 O4'
_chemical_formula_sum            'C8 H12 O4'
_chemical_formula_weight         172.18
_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                 104.486(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4523(8)
_cell_length_b                   5.5812(5)
_cell_length_c                   10.7250(10)
_cell_measurement_reflns_used    1341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      3.01
_cell_volume                     431.90(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'high brilliance Incoatec Microfocus Source '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5433
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0513P)^2^+0.0241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                1364
_reflns_number_total             1976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403461b_si_002.cif
_cod_data_source_block           mo_o31rb48_0m
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1513394