Exploring the Scope of Asymmetric Synthesis of β-Hydroxy-γ-lactams via Noyori-type Reductions.
Lynch, Denis; Deasy, Rebecca E.; Clarke, Leslie-Ann; Slattery, Catherine N.; Khandavilli, U. B. Rao; Lawrence, Simon E.; Maguire, Anita R.; Magnus, Nicholas A.; Moynihan, Humphrey A.; Organic letters 18 (2016) 4978–4981; doi:10.1021/acs.orglett.6b02416

data_1555767
_publ_section_title
;
 Exploring the Scope of Asymmetric Synthesis of \b-Hydroxy-\g-lactams via
 Noyori-type Reductions.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4978
_journal_page_last               4981
_journal_paper_doi               10.1021/acs.orglett.6b02416
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3836(3)
_cell_length_b                   31.775(2)
_cell_length_c                   9.5511(6)
_cell_measurement_reflns_used    3862
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      64.2453
_cell_measurement_theta_min      4.8332
_cell_volume                     1633.85(17)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker ACS Kappa APEX II DUO diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Incoatec Montel Multilayer Mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7369
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         4.84
_diffrn_source                   'Incoatec Microfocus X-ray Source I\mS'
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.239
_refine_ls_abs_structure_details
;
Flack x determined using 838 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0826
_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^)+(0.0882P)^2^+1.4305P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2324
_reflns_number_gt                2394
_reflns_number_total             2676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02416_si_002.cif
_cod_data_source_block           Compound_4d
_cod_database_code               1555767
_shelx_res_checksum              80988
_shelx_hkl_checksum              58167