Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of alpha,beta-unsaturated amides with ketones.
Lumby, Ralph J. R.; Joensuu, Pekka M.; Lam, Hon Wai; Organic letters 9 (2007) 4367–4370; doi:10.1021/ol701980e

data_1505571
_publ_section_title
;
 Diastereoselective intermolecular cobalt-catalyzed reductive aldol
 reactions of alpha,beta-unsaturated amides with ketones.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4367
_journal_page_last               4370
_journal_paper_doi               10.1021/ol701980e
_journal_volume                  9
_journal_year                    2007
_chemical_compound_source        'Ralph Lumby'
_chemical_formula_moiety         'C13 H25 N O3'
_chemical_formula_sum            'C13 H25 N O3'
_chemical_formula_weight         243.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.2200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.02370(10)
_cell_length_b                   10.0110(2)
_cell_length_c                   22.8384(5)
_cell_measurement_reflns_used    4741
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.9495
_cell_measurement_theta_min      2.2215
_cell_volume                     1376.20(5)
_computing_cell_refinement       Saint
_computing_data_reduction        Saint
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Shelxs Sheldrick'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'Phi and Omega scans'
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            16909
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         30.48
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.8706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method 'Evaporation of hexane solution'
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0649P)^2^+0.2287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                2857
_reflns_number_total             3988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol701980e-file005.cif
_cod_data_source_block           hl7010
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1505571