Phosphine-Catalyzed Diastereoselective Synthesis of β-Lactones from Disubstituted Ketenes and α-Chiral Oxyaldehydes.
Mondal, Mukulesh; Chen, Shi; Othman, Nabil; Wheeler, Kraig A.; Kerrigan, Nessan J.; The Journal of organic chemistry 80 (2015) 5789–5794; doi:10.1021/acs.joc.5b00869

data_4030997
_publ_section_title
;
 Phosphine-Catalyzed Diastereoselective Synthesis of \b-Lactones from
 Disubstituted Ketenes and \a-Chiral Oxyaldehydes.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5789
_journal_page_last               5794
_journal_paper_doi               10.1021/acs.joc.5b00869
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C10 H16 O4'
_chemical_formula_sum            'C10 H16 O4'
_chemical_formula_weight         200.23
_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
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 97.347(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7110(3)
_cell_length_b                   5.8434(2)
_cell_length_c                   15.8296(4)
_cell_measurement_reflns_used    7234
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.971
_cell_measurement_theta_min      2.884
_cell_volume                     1074.36(5)
_computing_cell_refinement       APEX2
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2012)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15715
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.337
_diffrn_reflns_theta_min         2.814
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0620P)^2^+0.3971P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.914
_reflns_number_gt                3482
_reflns_number_total             3761
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00869_si_002.cif
_cod_data_source_block           nker12
_cod_depositor_comments          'Adding full bibliography for 4030997.cif.'
_cod_database_code               4030997
_shelx_estimated_absorpt_t_min   0.786
_shelx_estimated_absorpt_t_max   0.864
_shelxl_version_number           2012-9
_shelx_res_checksum              31913
_shelx_hkl_checksum              26782