An organocatalytic Michael-cyclization cascade of 4-oxa-alpha,beta-unsaturated carboxylic acids with aldehydes: facile synthesis of chiral gamma-lactols and trisubstituted gamma-lactones
Jun-Bing Lin; Shi-Ming Xu; Ji-Kang Xie; Hong-Yu Li; Peng-Fei Xu; Chem.Commun. 51 (2015) 3596–; doi:10.1039/C4cc09686J

data_7116552
_publ_section_title
;
 An organocatalytic Michael-cyclization cascade of
 4-oxa-alpha,beta-unsaturated carboxylic acids with aldehydes: facile
 synthesis of chiral gamma-lactols and trisubstituted gamma-lactones
;
_journal_name_full               Chem.Commun.
_journal_page_first              3596
_journal_paper_doi               10.1039/C4cc09686J
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H18 O4'
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_audit_update_record
;
2014-11-23 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.779(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6167(3)
_cell_length_b                   25.0791(11)
_cell_length_c                   11.3191(6)
_cell_measurement_reflns_used    1149
_cell_measurement_temperature    294.68(10)
_cell_measurement_theta_max      22.2370
_cell_measurement_theta_min      3.9640
_cell_volume                     1594.28(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.68(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -8.00   19.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000 -120.0000 18

  2 omega    2.00   92.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000  -90.0000 60

  3 omega   31.00   58.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -99.0000 -150.0000 18

  4 omega    2.00   92.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000    0.0000 60
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0457676000
_diffrn_orient_matrix_UB_12      -0.0005515000
_diffrn_orient_matrix_UB_13      0.0587176000
_diffrn_orient_matrix_UB_21      -0.1177047000
_diffrn_orient_matrix_UB_22      0.0003730000
_diffrn_orient_matrix_UB_23      0.0218686000
_diffrn_orient_matrix_UB_31      -0.0024318000
_diffrn_orient_matrix_UB_32      -0.0282740000
_diffrn_orient_matrix_UB_33      -0.0008520000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6897
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.60
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5167
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                3315
_reflns_number_total             5167
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc09686j2.cif
_cod_data_source_block           lingjb1118
_cod_database_code               7116552
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C29(H29), C31(H31), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B), C28(H28A,H28B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C35(H35),
  C36(H36), C37(H37), C38(H38), C39(H39)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'