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_4034340
_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         'C26 H30 N2 O3'
_chemical_formula_sum            'C26 H30 N2 O3'
_chemical_formula_weight         418.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 94.265(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.060(2)
_cell_length_b                   9.1934(17)
_cell_length_c                   22.324(5)
_cell_measurement_reflns_used    4125
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.97
_cell_measurement_theta_min      2.40
_cell_volume                     2263.6(8)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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  0.1332
_diffrn_reflns_av_unetI/netI     0.1734
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21754
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.748
_diffrn_reflns_theta_min         2.397
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.6463
_exptl_absorpt_correction_T_min  0.5201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1609 before and 0.1263 after correction.
The Ratio of minimum to maximum transmission is 0.8047.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_coef       0.025(4)
_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   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         8500
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0810
_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^)+(0.0889P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1886
_refine_ls_wR_factor_ref         0.2241
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                5462
_reflns_number_total             8500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00320_si_003.cif
_cod_data_source_block           mo_ocjg100818_0m
_cod_database_code               4034340
_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:
 C00D(H00D), C00I(H00I), C00K(H00K), C00L(H00L), C00U(H00U), C00X(H00X)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00B), C00S(H00G,H00H), C00Z(H00C,H00E), C01B(H01R,H01S), C01D(H01B,
 H01C), C01H(H01Z,HA), C01I(H01D,H01F), C01J(H01,HB), C01K(H01G,H01H),
 C01N(H0AA,HC), C01O(H1AA,HD), C01P(H01M,H01N)
2.c Aromatic/amide H refined with riding coordinates:
 N008(H008), N00A(H00F), C00O(H00O), C00R(H00R), C00T(H00T), C00V(H00V),
 C00W(H00W), C00Y(H00Y), C010(H010), C012(H012), C014(H014), C016(H016),
 C018(H018), C019(H019), C01A(H01A), C01C(H01T), C01E(H01E), C01L(H01L)
2.d Idealised Me refined as rotating group:
 C01F(H01U,H01V,H01W), C01G(H01X,H01Y,H), C01M(H01I,H01J,H01K), C01Q(H01O,H01P,
 H01Q)
;
_shelx_res_checksum              30777
_shelx_hkl_checksum              80499
_olex2_submission_special_instructions 'No special instructions were received'