Asymmetric Synthesis of Ethoxydienamines in Superbasic Medium Mediated by Chiral Sulfinyl Group
Marco Blangetti; Gianluca Croce; Annamaria Deagostino; Eleonora Mussano; Cristina Prandi; Paolo Venturello; Journal of Organic Chemistry 76 (2011) 1814–1820; doi:10.1021/jo1024943

data_4026141
_publ_contact_author_address
;Dipartimento di Chimica Generale e Chimica Organica, Universit\`a di Torino,
Corso Massimo D?Azeglio, 48, I-10125 Torino, Italy
;
_publ_contact_author_email       cristina.prandi@unito.it
_publ_contact_author_name        'Cristina Prandi'
_publ_section_title
;
 Asymmetric Synthesis of Ethoxydienamines in Superbasic Medium Mediated by
 Chiral Sulfinyl Group
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1814
_journal_page_last               1820
_journal_paper_doi               10.1021/jo1024943
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C18 H24 N O2 S'
_chemical_name_systematic
;
 ?
;
_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                   8.0114(12)
_cell_length_b                   12.5034(14)
_cell_length_c                   18.835(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1886.7(4)
_computing_cell_refinement       'CrysAlis RED 1.171.26 (OXford Diffraction)'
_computing_data_collection       'CrysAlis CCD 1.171.26 (OXford Diffraction)'
_computing_data_reduction        'CrysAlis RED 1.171.26 (OXford Diffraction)'
_computing_molecular_graphics
'ORTEP3 for Windows  (Farrugia, L. J., 1997) '
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2007)'
_computing_structure_solution    'Sir2008 (Burla, 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.3910
_diffrn_reflns_av_sigmaI/netI    0.2910
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            57507
_diffrn_reflns_theta_full        31.91
_diffrn_reflns_theta_max         31.91
_diffrn_reflns_theta_min         4.43
_exptl_absorpt_coefficient_mu    0.309
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             864
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.20(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         6116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.3301
_refine_ls_R_factor_gt           0.0926
_refine_ls_shift/su_max          0.135
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.2070
_reflns_number_gt                1743
_reflns_number_total             6116
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1024943_si_003.cif
_cod_data_source_block           mar1abs
_cod_original_formula_sum        'C18 H24 N1 O2 S1'
_cod_database_code               4026141