Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids
Cantú-Reyes, Margarita; Alvarado-Beltrán, Isabel; Ballinas-Indilí, Ricardo; Álvarez-Toledano, Cecilio; Hernández-Rodríguez, Marcos; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01853C

data_7155866
_publ_section_title
;
 Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals
 with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation,
 a one-pot protocol to obtain chiral \b-amino acids
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01853C
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_compound_source        'Organic synthesis'
_chemical_formula_moiety         'C15 H23 N O3 S'
_chemical_formula_sum            'C15 H23 N O3 S'
_chemical_formula_weight         297.40
_chemical_melting_point          414.5(15)
_chemical_name_systematic
'(R,R)-3-(2-methylpropane-2-sulfinylamino)-2,2-dimethyl-3-phenylpropanoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc1n4blq
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-19 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.908(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.7982(16)
_cell_length_b                   6.0423(5)
_cell_length_c                   14.3040(12)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.16
_cell_volume                     1589.7(2)
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_collection       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12570
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.311
_diffrn_reflns_theta_min         3.157
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    1.867
_exptl_absorpt_correction_T_max  0.8892
_exptl_absorpt_correction_T_min  0.7874
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SHELXTL (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       Prism
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hexane '
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 1028 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0252P)^2^+1.7462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2647
_reflns_number_total             2874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01853c2.cif
_cod_data_source_block           266HRM16
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '413-416' was changed to '414.5(15)'
- the average value was taken and precision was estimated.

'_exptl_absorpt_correction_type' value 'Analytical' changed to
'analytical' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7155866
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.702
_shelx_estimated_absorpt_t_max   0.856
_shelx_res_checksum              90109
_shelx_hkl_checksum              81565