Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (-)-Paroxetine.
Porey, Arka; Santra, Surojit; Guin, Joyram; The Journal of organic chemistry 84 (2019) 5313–5327; doi:10.1021/acs.joc.9b00320

data_4034338
_publ_section_title
;
 Highly Enantioselective Synthesis of Functionalized Glutarimide Using
 Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of
 (-)-Paroxetine.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5313
_journal_page_last               5327
_journal_paper_doi               10.1021/acs.joc.9b00320
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H30 N2 O5 S'
_chemical_formula_sum            'C27 H30 N2 O5 S'
_chemical_formula_weight         494.59
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3800(10)
_cell_length_b                   11.2730(11)
_cell_length_c                   25.440(3)
_cell_measurement_reflns_used    8273
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.57
_cell_measurement_theta_min      2.31
_cell_volume                     2690.0(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.27
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.314
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1546 before and 0.0955 after correction.
The Ratio of minimum to maximum transmission is 0.5518.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       needle
_exptl_crystal_F_000             1048
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0554P)^2^+0.7697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4196
_reflns_number_total             5502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00320_si_004.cif
_cod_data_source_block           mo_jgog251018_0m
_cod_original_cell_volume        2690.1(5)
_cod_database_code               4034338
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00B(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00J(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), N005(H005), C00G(H00G), C00H(H00H), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00U(H00U), C00V(H00V), C00W(H00W)
2.d Idealised Me refined as rotating group:
 C00X(H00F,H00I,H00J), C00Y(H00P,H00T,H00X), C00Z(H00Y,H,HA)
;
_shelx_res_checksum              67730
_shelx_hkl_checksum              87959
_olex2_submission_special_instructions 'No special instructions were received'