Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using phase-transfer catalytic alkylation.
Lee, Myungmo; Lee, Young-Ju; Park, Eunyoung; Park, Yohan; Ha, Min Woo; Hong, Suckchang; Lee, Yeon-Ju; Kim, Taek-Soo; Kim, Mi-Hyun; Park, Hyeung-Geun; Organic & biomolecular chemistry 11 (2013) 2039–2046; doi:10.1039/c3ob27089k

data_7152830
_publ_section_title
;
 Highly enantioselective synthesis of 5-phenyl-2-alkylprolines using
 phase-transfer catalytic alkylation.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2039
_journal_page_last               2046
_journal_paper_doi               10.1039/c3ob27089k
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C22 H24 Br N O2'
_chemical_formula_sum            'C22 H24 Br N O2'
_chemical_formula_weight         414.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.678(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   12.297(3)
_cell_length_b                   5.9174(9)
_cell_length_c                   14.699(3)
_cell_measurement_reflns_used    5550
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.35
_cell_volume                     1029.8(4)
_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_temperature      295
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9888
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.016
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_correction_T_min  0.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             428.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.210
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1712 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.009(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     238
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                2102
_reflns_number_total             4281
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c3ob27089k.txt
_cod_data_source_block           yj292a
_cod_original_cell_volume        1029.8(3)
_cod_database_code               7152830