Effective 1,5-stereocontrol in Pd(0)/InI promoted reactions of chiral N-Ts-4-vinylazetidin-2-ones with aldehydes. An efficient entry into nonracemic semi-protected (3Z)-2,6-anti-enediols
Urszula K. Klimczak; Bartosz K. Zambron; Chem.Commun. 51 (2015) 6796–; doi:10.1039/C5cc01485A

data_7116941
_publ_section_title
;
 Effective 1,5-stereocontrol in Pd(0)/InI promoted reactions of chiral
 N-Ts-4-vinylazetidin-2-ones with aldehydes. An efficient entry into
 nonracemic semi-protected (3Z)-2,6-anti-enediols
;
_journal_name_full               Chem.Commun.
_journal_page_first              6796
_journal_paper_doi               10.1039/C5cc01485A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C28.84 H42.57 N O6 S Si'
_chemical_formula_sum            'C28.84 H42.57 N O6 S Si'
_chemical_formula_weight         559.50
_chemical_melting_point          396.6(5)
_chemical_name_systematic
'(2R*,6S*,Z)-6-hydroxy-6-(4-methoxyphenyl)-N-tosyl-2-(triisopropylsilyloxy)hex-3-enamide '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-02-09 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.208(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.627(2)
_cell_length_b                   13.4083(19)
_cell_length_c                   15.769(2)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      4.45
_cell_volume                     3100.7(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.887
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13497
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         4.450
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.622
_exptl_absorpt_correction_T_max  0.6970
_exptl_absorpt_correction_T_min  0.5900
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/Ethyl acetate'
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1831
_refine_ls_R_factor_gt           0.1077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1548P)^2^+11.5689P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3289
_refine_ls_wR_factor_ref         0.3733
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2931
_reflns_number_total             4970
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc01485a2.cif
_cod_data_source_block           B2F145d_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '396.1-397.2' was changed to
'396.6(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_formula_sum        'C28.84 H42.57 N O6 S Si '
_cod_database_code               7116941
_shelx_estimated_absorpt_t_min   0.590
_shelx_estimated_absorpt_t_max   0.697
_shelxl_version_number           2014-3
_shelx_res_checksum              3778