Multiple Absolute Stereocontrol in Cascade Lactone Formation via Dynamic Kinetic Resolution Driven by the Asymmetric Transfer Hydrogenation of Keto Acids with Oxo-Tethered Ruthenium Catalysts.
Touge, Taichiro; Sakaguchi, Kazuhiko; Tamaki, Nao; Nara, Hideki; Yokozawa, Tohru; Matsumura, Kazuhiko; Kayaki, Yoshihito; Journal of the American Chemical Society 141 (2019) 16354–16361; doi:10.1021/jacs.9b07297

data_4127671
_publ_section_title
;
 Multiple Absolute Stereocontrol in Cascade Lactone Formation via Dynamic
 Kinetic Resolution Driven by the Asymmetric Transfer Hydrogenation of
 Keto Acids with Oxo-Tethered Ruthenium Catalysts.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16354
_journal_page_last               16361
_journal_paper_doi               10.1021/jacs.9b07297
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H18 O3'
_chemical_formula_sum            'C19 H18 O3'
_chemical_formula_weight         294.33
_chemical_name_systematic
;
(1S,3aR,9bS)-9-Methoxy-1-phenyl-3a,4,5,9b-tetrahydronaphtho[2,1-b]furan-2(1H)-one
;
_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'
_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     dual
_audit_creation_date             2019-02-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.70360(10)
_cell_length_b                   6.16330(10)
_cell_length_c                   15.5653(2)
_cell_measurement_reflns_used    9301
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.9220
_cell_measurement_theta_min      2.8190
_cell_volume                     738.984(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -121.00  -8.00   0.50    0.12    --  -39.70 -38.00 -30.00  226
  2  \w    -43.00  41.00   0.50    0.12    --  -39.70  38.00 124.00  168
  3  \w    -43.00 -13.00   0.50    0.48    --  -94.50  38.00 124.00   60
  4  \w   -175.00 -63.00   0.50    0.48    --  -94.50 -38.00 -30.00  224
  5  \w     84.00 178.00   0.50    0.48    --  116.00  38.00 124.00  188
  6  \w   -115.00 -12.00   0.50    0.12    --  -39.70 -57.00-150.00  206
  7  \w     60.00 121.00   0.50    0.12    --   39.70 178.00 -90.00  122
  8  \w     13.00 115.00   0.50    0.12    --   39.70  57.00 -60.00  204
  9  \w   -174.00 -65.00   0.50    0.48    --  -94.50 -44.00-125.03  218
 10  \w   -170.00 -59.00   0.50    0.48    --  -94.50 -79.00-160.51  222
 11  \w   -169.00 -67.00   0.50    0.48    --  -94.50 -58.00-133.45  204
 12  \w   -170.00 -62.00   0.50    0.48    --  -94.50 -71.00 175.29  216
 13  \w   -170.00 -65.00   0.50    0.48    --  -94.50 -61.00 -90.00  210
 14  \w    -71.00 -19.00   0.50    0.48    --  -94.50  61.00 -60.00  104
 15  \w   -170.00 -60.00   0.50    0.48    --  -94.50 -76.00-136.27  220
 16  \w    -51.00 -15.00   0.50    0.48    --  -94.50  45.00 -60.00   72
 17  \w    -51.00 -15.00   0.50    0.48    --  -94.50  45.00 -90.00   72
 18  \w   -170.00 -60.00   0.50    0.48    --  -94.50 -77.00-120.00  220
 19  \w   -170.00 -65.00   0.50    0.48    --  -94.50 -61.00-120.00  210
 20  \w   -170.00 -63.00   0.50    0.48    --  -94.50 -70.00-154.78  214
 21  \w    100.00 178.00   0.50    0.48    --  116.00 111.00 -30.00  156
 22  \w     42.00  71.00   0.50    0.48    --  116.00 -61.00 -90.00   58
 23  \w     42.00  71.00   0.50    0.48    --  116.00 -61.00-150.00   58
 24  \w     36.00 109.00   0.50    0.48    --  116.00 -94.00   0.00  146
 25  \w     42.00 106.00   0.50    0.48    --  116.00 -77.00-150.00  128
 26  \w     87.00 178.00   0.50    0.48    --  116.00  45.00-180.00  182
 27  \w     36.00 109.00   0.50    0.48    --  116.00 -94.00 -30.00  146
 28  \w     42.00 106.00   0.50    0.48    --  116.00 -77.00  60.00  128
 29  \w     81.00 178.00   0.50    0.48    --  116.00  77.00 -90.00  194
 30  \w     87.00 178.00   0.50    0.48    --  116.00  61.00-139.00  182
 31  \w     36.00 109.00   0.50    0.48    --  116.00 -94.00-120.00  146
 32  \w     42.00  71.00   0.50    0.48    --  116.00 -61.00   0.00   58
 33  \w     79.00 178.00   0.50    0.48    --  116.00  30.00 -60.00  198
 34  \w     87.00 178.00   0.50    0.48    --  116.00  61.00-120.00  182
 35  \w     81.00 178.00   0.50    0.48    --  116.00  77.00-120.00  194
 36  \w     36.00 111.00   0.50    0.48    --  116.00-111.00  90.00  150
 37  \w     86.00 178.00   0.50    0.48    --  116.00  63.00 132.01  184
 38  \w     42.00  71.00   0.50    0.48    --  116.00 -61.00-180.00   58
 39  \w     87.00 178.00   0.50    0.48    --  116.00  61.00-150.00  182
 40  \w     87.00 178.00   0.50    0.48    --  116.00  61.00-180.00  182
 41  \w     81.00 178.00   0.50    0.48    --  116.00  77.00-180.00  194
 42  \w     42.00  71.00   0.50    0.48    --  116.00 -61.00 120.00   58
 43  \w    100.00 178.00   0.50    0.48    --  116.00 111.00 150.00  156
 44  \w     42.00  71.00   0.50    0.48    --  116.00 -61.00  60.00   58
 45  \w     42.00  71.00   0.50    0.48    --  116.00 -61.00-120.00   58
 46  \w   -115.00 -31.00   0.50    0.12    --  -39.70 -57.00  90.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0335063000
_diffrn_orient_matrix_UB_12      -0.0816024000
_diffrn_orient_matrix_UB_13      0.0918239000
_diffrn_orient_matrix_UB_21      0.1866550000
_diffrn_orient_matrix_UB_22      -0.0889568000
_diffrn_orient_matrix_UB_23      0.0053504000
_diffrn_orient_matrix_UB_31      0.0633887000
_diffrn_orient_matrix_UB_32      0.2190171000
_diffrn_orient_matrix_UB_33      0.0364858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15067
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.268
_diffrn_reflns_theta_min         2.839
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0527
_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^)+(0.1090P)^2^+0.0414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3023
_reflns_number_total             3072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07297_si_008.cif
_cod_data_source_block           exp_37
_cod_database_code               4127671
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
0145b7c1945035fe4ea2f3cd3be52372f6071843d09
;
_diffrn_oxdiff_digest_hkl
;
0172daa18f80b871c3b42843a427dbec75f3bf
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C18(H18), C17(H17), C5(H5), C16(H16), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              95494
_shelx_hkl_checksum              37094
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.844
_oxdiff_exptl_absorpt_empirical_full_min 0.650