A Highly Efficient Solvent-Free Asymmetric Direct Aldol Reaction Organocatalyzed by Recoverable (S)-Binam-l-Prolinamides. ESI-MS Evidence of the Enamine-Iminium Formation
Gabriela Guillena; María del Carmen Hita; Carmen Nájera; Santiago F. Viózquez; Journal of Organic Chemistry 73 (2008) 5933–5943; doi:10.1021/jo800773q

data_4023584
_publ_section_title
;
 A Highly Efficient Solvent-Free Asymmetric Direct Aldol Reaction
 Organocatalyzed by Recoverable (S)-Binam-l-Prolinamides.
 ESI-MS Evidence of the Enamine-Iminium Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5933
_journal_page_last               5943
_journal_paper_doi               10.1021/jo800773q
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H23 N3 O'
_chemical_formula_sum            'C25 H23 N3 O'
_chemical_formula_weight         381.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   8.2321(5)
_cell_length_b                   13.9353(8)
_cell_length_c                   17.6655(11)
_cell_measurement_reflns_used    3133
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.6
_cell_measurement_theta_min      2.73
_cell_volume                     2026.5(2)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;SIR92 (Altomare, Cascarano, Giacovazzo and Guagliardi, 
J. Appl. Crystallogr. 1993, 26, 343-350.' 
;
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17106
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0711P)^2^+0.1910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                1680
_reflns_number_total             2073
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo800773q-File002.cif
_cod_data_source_block           x
_cod_database_code               4023584