Reverse regioselectivity in Pd(0)/InI-mediated allylation of aldehydes with ε-amido-allylindiums generated from β-lactams. A new entry to non-racemic highly substituted γ-butyrolactones.
Klimczak, Urszula Katarzyna; Staszewska-Krajewska, Olga; Zambroń, Bartosz Krzysztof; RSC Adv.  (2016) –; doi:10.1039/C6RA00517A

data_7224478
_publ_section_title
;
 Reverse regioselectivity in Pd(0)/InI-mediated allylation of aldehydes
 with \e-amido-allylindiums generated from \b-lactams. A new entry to
 non-racemic highly substituted \g-butyrolactones.
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA00517A
_journal_year                    2016
_chemical_formula_moiety         'C20.50 H29.50 O3 Si, C21 H32 O3 Si'
_chemical_formula_sum            'C41.5 H61.5 O6 Si2'
_chemical_formula_weight         712.58
_chemical_melting_point          347.3(4)
_chemical_name_systematic
(3R*,4R*,5R*)-5-phenyl-3-(triisopropylsilyloxy)-4-vinyldihydrofuran-2(3H)-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-10-06 deposited with the CCDC.
2016-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                84.881(3)
_cell_angle_beta                 77.283(3)
_cell_angle_gamma                88.864(3)
_cell_formula_units_Z            2
_cell_length_a                   11.9536(5)
_cell_length_b                   13.6314(6)
_cell_length_c                   13.8816(6)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      3.25
_cell_volume                     2197.64(17)
_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 0.937
_diffrn_measured_fraction_theta_max 0.962
_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  0.0574
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_laue_measured_fraction_full 0.937
_diffrn_reflns_laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46104
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.255
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.050
_exptl_absorpt_correction_T_max  0.8590
_exptl_absorpt_correction_T_min  0.7680
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             773
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.149
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         7468
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1396P)^2^+0.1952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5047
_reflns_number_total             7468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra00517a2.cif
_cod_data_source_block           U34_A_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '346.9-347.7' was changed to
'347.3(4)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_formula_sum        'C41.50 H61.50 O6 Si2'
_cod_database_code               7224478
_shelx_estimated_absorpt_t_min   0.768
_shelx_estimated_absorpt_t_max   0.859
_shelxl_version_number           2014-3
_shelx_res_checksum              61105