Asymmetric Vinylogous Mannich Reaction of Silyloxy Furans with N-tert-Butanesulfinyl Ketimines.
Rao, V. U. Bhaskara; Jadhav, Amol P.; Garad, Dnyaneshwar; Singh, Ravi P.; Organic letters 16 (2014) 648–651; doi:10.1021/ol4037117

data_1513460
_publ_section_title
;
 Asymmetric Vinylogous Mannich Reaction of Silyloxy Furans with
 N-tert-Butanesulfinyl Ketimines.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              648
_journal_page_last               651
_journal_paper_doi               10.1021/ol4037117
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H36 N2 O4 S'
_chemical_formula_sum            'C37 H36 N2 O4 S'
_chemical_formula_weight         604.75
_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                   9.2689(3)
_cell_length_b                   11.8049(3)
_cell_length_c                   29.3310(8)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.60
_cell_volume                     3209.35(16)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'BRUKER SMART APEX2'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\f and \w 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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            28765
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0508P)^2^+0.4644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                6653
_reflns_number_total             7967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4037117_si_003.cif
_cod_data_source_block           rps1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
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_cod_database_code               1513460