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_4127681
_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
;
(1R,3aS,9bR)-8-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             2019-02-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.11.30 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5622)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.401(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8340(2)
_cell_length_b                   5.85050(10)
_cell_length_c                   12.9552(2)
_cell_measurement_reflns_used    7258
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7670
_cell_measurement_theta_min      3.4810
_cell_volume                     727.97(2)
_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      100.00(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 0.983
_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    -26.00  43.00   0.50    0.37    --  -39.63  19.00  60.00  138
  2  \w    -45.00  26.00   0.50    0.37    --   39.63 -19.00  30.00  142
  3  \w     80.00 178.00   0.50    1.48    --  114.32  77.00 133.00  196
  4  \w     77.00 178.00   0.50    1.48    --  114.32  30.00 -60.00  202
  5  \w     85.00 178.00   0.50    1.48    --  114.32  61.00-180.00  186
  6  \w     80.00 178.00   0.50    1.48    --  114.32  77.00-150.00  196
  7  \w     77.00 178.00   0.50    1.48    --  114.32  30.00 -90.00  202
  8  \w     77.00 178.00   0.50    1.48    --  114.32  30.00  90.00  202
  9  \w     60.00 122.00   0.50    0.37    --   39.63 178.00 -90.00  124
 10  \w     60.00 122.00   0.50    0.37    --   39.63 178.00  30.00  124
 11  \w     60.00 122.00   0.50    0.37    --   39.63 178.00  60.00  124
 12  \w    -45.00  26.00   0.50    0.37    --   39.63 -19.00-150.00  142
 13  \w     39.00 106.00   0.50    1.48    --  114.32 -77.00   7.00  134
 14  \w     39.00 106.00   0.50    1.48    --  114.32 -77.00  90.00  134
 15  \w     39.00 106.00   0.50    1.48    --  114.32 -77.00  60.00  134
 16  \w     37.00 117.00   0.50    1.48    --  114.32-125.00   0.00  160
 17  \w     39.00  71.00   0.50    1.48    --  114.32 -61.00-150.00   64
 18  \w     34.00 109.00   0.50    1.48    --  114.32 -94.00-150.00  150
 19  \w     39.00 106.00   0.50    1.48    --  114.32 -77.00 -90.00  134
 20  \w     39.00  71.00   0.50    1.48    --  114.32 -61.00-180.00   64
 21  \w     37.00 117.00   0.50    1.48    --  114.32-125.00  90.00  160
 22  \w     39.00  71.00   0.50    1.48    --  114.32 -61.00 150.00   64
 23  \w    -74.00  36.00   0.50    0.37    --  -39.63  77.00 133.00  220
 24  \w    -51.00 -15.00   0.50    1.48    --  -94.50  45.00  60.00   72
 25  \w    -51.00 -15.00   0.50    1.48    --  -94.50  45.00 -30.00   72
 26  \w   -106.00 -19.00   0.50    1.48    --  -94.50  77.00 133.00  174
 27  \w   -115.00 -12.00   0.50    0.37    --  -39.63 -57.00  60.00  206
 28  \w   -115.00  -5.00   0.50    0.37    --  -39.63 -77.00   7.00  220
 29  \w   -115.00  -5.00   0.50    0.37    --  -39.63 -77.00 120.00  220
 30  \w   -115.00  -5.00   0.50    0.37    --  -39.63 -77.00-120.00  220
 31  \w   -115.00 -12.00   0.50    0.37    --  -39.63 -57.00-120.00  206
 32  \w   -115.00  -5.00   0.50    0.37    --  -39.63 -77.00 150.00  220
 33  \w   -170.00 -60.00   0.50    1.48    --  -94.50 -77.00   7.00  220
 34  \w   -174.00 -65.00   0.50    1.48    --  -94.50 -45.00 -90.00  218
 35  \w   -170.00 -65.00   0.50    1.48    --  -94.50 -61.00  60.00  210
 36  \w   -170.00 -67.00   0.50    1.48    --  -94.50 -77.00 -90.00  206
 37  \w   -174.00 -65.00   0.50    1.48    --  -94.50 -45.00 -60.00  218
 38  \w   -170.00 -60.00   0.50    1.48    --  -94.50 -77.00 150.00  220
 39  \w   -170.00 -60.00   0.50    1.48    --  -94.50 -77.00  60.00  220
 40  \w   -170.00 -60.00   0.50    1.48    --  -94.50 -77.00-150.00  220
 41  \w   -170.00 -60.00   0.50    1.48    --  -94.50 -77.00 120.00  220
;
_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      0.0392571000
_diffrn_orient_matrix_UB_12      -0.0729546000
_diffrn_orient_matrix_UB_13      0.1168685000
_diffrn_orient_matrix_UB_21      0.0774657000
_diffrn_orient_matrix_UB_22      -0.2096882000
_diffrn_orient_matrix_UB_23      -0.0307281000
_diffrn_orient_matrix_UB_31      0.1348460000
_diffrn_orient_matrix_UB_32      0.1416989000
_diffrn_orient_matrix_UB_33      0.0147364000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13484
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.560
_diffrn_reflns_theta_min         3.493
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1221 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0708P)^2^+0.2001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                2855
_reflns_number_total             2959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07297_si_002.cif
_cod_data_source_block           exp_31
_cod_depositor_comments
;

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.67(C19 H18 O3)'
_cod_original_formula_sum        'C12.67 H12 O2'
_cod_original_formula_units_Z    3
_cod_original_formula_weight     196.22
_cod_database_code               4127681
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
017dfa8cf32ece7bf48236a016d48437d2069584692
;
_diffrn_oxdiff_digest_hkl
;
01d8bd68c21b003390214becceb64027926aa9
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C009(H009), C00K(H00L), C00L(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00E), C00M(H00N,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F),
 C00G(H00G), C00J(H00K)
2.d Idealised Me refined as rotating group:
 C00I(H00H,H00I,H00J)
;
_shelx_res_checksum              55344
_shelx_hkl_checksum              69616
_ins_header
;
TITL exp_31 in P2(1)/m 
REM P2(1)/m (#11 in standard setting)
CELL 1.54184   9.833965   5.850472  12.955222  90.0000 102.4011  90.0000
ZERR    3.00   0.000153   0.000084   0.000227   0.0000   0.0016   0.0000
LATT  1
SYMM -x, y+1/2,-z 
SFAC C H N O
UNIT 33.00 30.00 3.00 3.00
TREF
HKLF 4
END
;
_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 1.559
_oxdiff_exptl_absorpt_empirical_full_min 0.705