Reformatsky Reaction to Alkynyl N- tert-Butanesulfinyl Imines: Lewis Acid Controlled Stereodivergent Synthesis of β-Alkynyl-β-Amino Acids.
Fernández-Sánchez, Luis; Fernández-Salas, José A; Maestro, M. Carmen; García Ruano, Jose L; The Journal of organic chemistry 83 (2018) 12903–12910; doi:10.1021/acs.joc.8b01918

data_4035406
_publ_section_title
;
 Reformatsky Reaction to Alkynyl N- tert-Butanesulfinyl Imines: Lewis Acid
 Controlled Stereodivergent Synthesis of \b-Alkynyl-\b-Amino Acids.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12903
_journal_page_last               12910
_journal_paper_doi               10.1021/acs.joc.8b01918
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H31 N O3 S Si'
_chemical_formula_weight         345.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7993(4)
_cell_length_b                   16.3444(11)
_cell_length_c                   21.7331(14)
_cell_measurement_reflns_used    4323
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.3248
_cell_measurement_theta_min      2.6628
_cell_volume                     2060.0(2)
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10156
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.645
_refine_ls_abs_structure_details
;

Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0647P)^2^+2.0021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                3500
_reflns_number_total             3745
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01918_si_002.cif
_cod_data_source_block           00544CarmenMaestro
_cod_database_code               4035406
_shelx_res_checksum              88252
_shelx_hkl_checksum              95160