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_7159322
_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         'C18 H28 O5 Si'
_chemical_formula_structural     'butyrolactyl-C6H2-3,5-(OMe)2, 4-OSi-Me2,tBu'
_chemical_formula_sum            'C18 H28 O5 Si'
_chemical_formula_weight         352.49
_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
_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                 91.051(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   10.5484(5)
_cell_length_c                   24.6032(13)
_cell_measurement_reflns_used    4489
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      30.2930
_cell_measurement_theta_min      2.0900
_cell_volume                     1866.03(17)
_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 0.991
_diffrn_measured_fraction_theta_max 0.775
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.775
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13116
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.682
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.796
_diffrn_reflns_theta_min         2.101
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       rod
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.24(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7980
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0495P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.846
_reflns_Friedel_fraction_max     0.579
_reflns_number_gt                6444
_reflns_number_total             7980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00563a2.cif
_cod_data_source_block           stepheno10
_cod_depositor_comments
'Adding full bibliography for 7159321--7159322.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159322
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              44368