E,Z-Stereodivergent Synthesis of N-Tosyl α,β-Dehydroamino Esters via a Mukaiyama-Michael Addition
Espinosa, Miguel; García Ortiz, Andrea; Blay, Gonzalo; Cardona, Luz; Muñoz, Carmen; Pedro, Jose R.; RSC Adv.  (2016) –; doi:10.1039/C5RA27354D

data_7224100
_publ_section_title
;
 E,Z-Stereodivergent Synthesis of N-Tosyl \a,\b-Dehydroamino Esters via a
 Mukaiyama-Michael Addition
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA27354D
_journal_year                    2016
_chemical_formula_sum            'C23 H27 N O6 S'
_chemical_formula_weight         445.52
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2015-12-14 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 125.4390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1470(2)
_cell_length_b                   18.6590(3)
_cell_length_c                   14.8300(2)
_cell_measurement_reflns_used    5409
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2287.61(7)
_computing_cell_refinement       'HKL DENZO'
_computing_data_collection       COLLECT
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0190
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10307
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9858
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1916P)^2^+1.2399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1572
_reflns_number_gt                4235
_reflns_number_total             5237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra27354d2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7224100