Intramolecular Michael reaction of tert-butylsulfinyl ketimines: asymmetric synthesis of 3-substituted indanones.
Fustero, Santos; Rodríguez, Elsa; Herrera, Lidia; Asensio, Amparo; Maestro, Miguel A.; Barrio, Pablo; Organic letters 13 (2011) 6564–6567; doi:10.1021/ol2028948

data_1502618
_publ_section_title
;
 Intramolecular Michael reaction of tert-butylsulfinyl ketimines:
 asymmetric synthesis of 3-substituted indanones.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6564
_journal_page_last               6567
_journal_paper_doi               10.1021/ol2028948
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H23 N O3 S'
_chemical_formula_sum            'C17 H23 N O3 S'
_chemical_formula_weight         321.42
_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                   9.6319(2)
_cell_length_b                   10.4594(3)
_cell_length_c                   16.7964(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1692.13(8)
_computing_cell_refinement       'SAINT V7.12A (Bruker 2004)'
_computing_data_collection       'Apex2 V.1.0-27(Bruker 2005)'
_computing_data_reduction        'SAINT and XPREP Version 6.14, 2003'
_computing_molecular_graphics    'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_publication_material  'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_structure_refinement  'SHELXL-97 in SHELXTL  ver. 6.12, 2001'
_computing_structure_solution    'SHELXS-97 in SHELXTL ver. 6.12, 2001'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17615
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9510
_exptl_absorpt_correction_T_min  0.9360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS program multi-scan
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.683
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.683
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1269P)^2^+0.7951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                3908
_reflns_number_total             4229
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2028948_si_002.cif
_cod_data_source_block           anc1
_cod_original_cell_volume        1692.14(8)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1502618