An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (-)-hapalosin.
Si, Chang-Mei; Shao, Lu-Ping; Mao, Zhuo-Ya; Zhou, Wen; Wei, Bang-Guo; Organic & biomolecular chemistry 15 (2017) 649–661; doi:10.1039/c6ob02523d

data_7155414
_publ_section_title
;
 An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones
 through a stereoselective tandem Barbier process: divergent syntheses of
 (3R,4S)-statines, (+)-preussin and (-)-hapalosin.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              649
_journal_page_last               661
_journal_paper_doi               10.1039/c6ob02523d
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C13 H23 N O4'
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
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;
2016-11-17 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_c                   25.561(4)
_cell_measurement_reflns_used    2461
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.623
_cell_measurement_theta_min      4.669
_cell_volume                     1475.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'Bruker SHELXTL'
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_diffrn_measured_fraction_theta_max 0.998
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -10
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_diffrn_reflns_limit_l_min       -24
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_description       prismatic
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_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EA/PE'
_exptl_crystal_size_max          0.200
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_refine_diff_density_min         -0.144
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_refine_ls_abs_structure_details
; 
 Flack x determined using 858 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_parameters     173
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.1452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2385
_reflns_number_total             2745
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02523d2.cif
_cod_data_source_block           cd16668
_cod_depositor_comments          'Adding full bibliography for 7155414.cif.'
_cod_database_code               7155414
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
_shelx_res_checksum              43529