Asymmetric Formal Carbonyl-Ene Reactions of Formaldehyde tert-Butyl Hydrazone with α-Keto Esters: Dual Activation by Bis-urea Catalysts
Ana Crespo-Peña; David Monge; Eloísa Martín-Zamora; Eleuterio Álvarez; Rosario Fernández; José M. Lassaletta; Journal of the American Chemical Society 134 (2012) 12912–12915; doi:10.1021/ja305209w

data_4118475
_publ_contact_author_address
;
  Dr. Jos\'e M. Lassaletta
     Instituto de Investigaciones Qu\'imicas, C.S.I.C-Universidad de Sevilla,
     Avd. Am\'erico Vespucio, 49., Isla de la Cartuja, E-41092 Sevilla,  Spain  
;
_publ_contact_author_email       jmlassa@iiq.csic.es
_publ_contact_author_fax         '+34 954 460565'
_publ_contact_author_name        'Prof. Jos\'e M. Lassaletta'
_publ_contact_author_phone       '+34 954 489563'
_publ_section_title
;
 Asymmetric Formal Carbonyl-Ene Reactions of Formaldehyde tert-Butyl
 Hydrazone with \a-Keto Esters: Dual Activation by Bis-urea Catalysts
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12912
_journal_page_last               12915
_journal_paper_doi               10.1021/ja305209w
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H12 O4 S'
_chemical_formula_sum            'C9 H12 O4 S'
_chemical_formula_weight         216.25
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   12.3447(4)
_cell_length_b                   12.3447(4)
_cell_length_c                   5.9591(3)
_cell_measurement_reflns_used    2858
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      3.30
_cell_volume                     786.45(5)
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
; 
 Bruker-Nonius X8kappa APEX II CCD area detector 
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7666
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         3.30
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9220
_exptl_absorpt_correction_T_min  0.8836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 program SADABS, Bruker (2001). 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1983
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0498P)^2^+0.1135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                1861
_reflns_number_total             1983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305209w_si_002_2.cif
_cod_data_source_block           (R)-7p
_cod_original_cell_volume        786.45(7)
_cod_database_code               4118475