Diastereoselective Reaction of Sulfoxonium Ylides, Aldehydes and Ketenes: An Approach to trans-γ-Lactones
Mukulesh Mondal; Han-Jen Ho; Nicholas J. Peraino; Melanie A. Gary; Kraig A. Wheeler; Nessan J. Kerrigan; Journal of Organic Chemistry 78 (2013) 4587–4593; doi:10.1021/jo4003213

data_4028199
_publ_section_title
;
 Diastereoselective Reaction of Sulfoxonium Ylides, Aldehydes and Ketenes:
 An Approach to trans-\g-Lactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4587
_journal_page_last               4593
_journal_paper_doi               10.1021/jo4003213
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C20 H21 N O4'
_chemical_formula_weight         339.37
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.150(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.5731(4)
_cell_length_b                   6.5305(2)
_cell_length_c                   31.5251(8)
_cell_measurement_temperature    100(2)
_cell_volume                     3403.04(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            44023
_diffrn_reflns_theta_full        67.73
_diffrn_reflns_theta_max         67.73
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.752
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1440
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     910
_refine_ls_number_reflns         11843
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.953
_refine_ls_shift/su_mean         0.075
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+8.1334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1750
_reflns_number_gt                8259
_reflns_number_total             11843
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4003213_si_002.cif
_cod_data_source_block           c:\frames\guest\nker07\work\nker07
_cod_original_cell_volume        3403.03(16)
_cod_original_sg_symbol_H-M      'P 1 21 1'
_cod_database_code               4028199