Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates.
Yoshida, Masanori; Masaki, Erika; Ikehara, Hiroto; Hara, Shoji; Organic & biomolecular chemistry 10 (2012) 5289–5297; doi:10.1039/c2ob25413a

data_7152413
_publ_section_title
;
 Enantioselective synthesis of gabapentin analogues via organocatalytic
 asymmetric Michael addition of \a-branched aldehydes to
 \b-nitroacrylates.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5289
_journal_page_last               5297
_journal_paper_doi               10.1039/c2ob25413a
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        '4,4-dimethylpyrrolidine-3-carboxylic acid'
_chemical_formula_moiety         'C13 H16 N2 O6 S'
_chemical_formula_sum            'C13 H16 N2 O6 S'
_chemical_formula_weight         328.34
_chemical_melting_point          430
_chemical_name_common
'N-nosyl 4,4-dimethylpyrrolidine-3-carboxylic acid'
_chemical_name_systematic
'(S)-N-(2-nitrophenylsulphonyl)-4,4-dimethylpyrrolidine-3-carboxylic acid'
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      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
_cell_angle_alpha                75.7436(14)
_cell_angle_beta                 72.7353(14)
_cell_angle_gamma                80.7840(13)
_cell_formula_units_Z            2
_cell_length_a                   7.5722(4)
_cell_length_b                   9.8018(5)
_cell_length_c                   10.6602(5)
_cell_measurement_reflns_used    6901
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.02
_cell_volume                     729.05(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo Ka'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7153
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344.00
_exptl_crystal_recrystallization_method 2-propanol/hexane
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
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_refine_diff_density_min         -0.330
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 2118 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5411
_refine_ls_number_restraints     3
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.3860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                5067
_reflns_number_total             5411
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c2ob25413a.txt
_cod_data_source_block           yoshida20120510
_cod_original_cell_volume        729.04(6)
_cod_database_code               7152413