An expedient copper-catalysed asymmetric synthesis of γ-lactones and γ-lactams. Application to the synthesis of lucidulactone A.
Ojo, O. Stephen; Hughes, David L.; Richards, Christopher J.; Organic & biomolecular chemistry 21 (2023) 4144–4149; doi:10.1039/d3ob00563a

data_7159321
_publ_section_title
;
 An expedient copper-catalysed asymmetric synthesis of &#x3b3;-lactones
 and &#x3b3;-lactams. Application to the synthesis of lucidulactone A.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4144
_journal_page_last               4149
_journal_paper_doi               10.1039/d3ob00563a
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_structural     4-MeO-C6H4-cyclo-(CHCH2OC(O)CH2)
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21
_chemical_name_systematic        (R)-6d
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-09 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.874(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0003(5)
_cell_length_b                   7.5875(3)
_cell_length_c                   9.1343(7)
_cell_measurement_reflns_used    6495
_cell_measurement_temperature    102(4)
_cell_measurement_theta_max      76.0720
_cell_measurement_theta_min      5.0140
_cell_volume                     464.28(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material
'SHELXL-2018/3 (Sheldrick, 2015b) and WINGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8875
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.479
_diffrn_reflns_theta_max         67.479
_diffrn_reflns_theta_min         5.060
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       plate
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 722 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1650
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0747P)^2^+0.0981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                1630
_reflns_number_total             1650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00563a2.cif
_cod_data_source_block           stepheno11a
_cod_depositor_comments
'Adding full bibliography for 7159321--7159322.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159321
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              86449