Phosphine-mediated enantioselective [4 + 1] annulations between ortho-quinone methides and Morita–Baylis–Hillman carbonates
Cheng, Yuyu; Fang, Zhiqiang; Li, Wenjun; Li, Pengfei; Organic Chemistry Frontiers 5 (2018) 2728–; doi:10.1039/C8QO00487K

data_1554358
_publ_section_title
;
 Phosphine-mediated enantioselective [4 + 1] annulations between
 ortho-quinone methides and Morita--Baylis--Hillman carbonates
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2728
_journal_paper_doi               10.1039/C8QO00487K
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H22 O5'
_chemical_formula_sum            'C20 H22 O5'
_chemical_formula_weight         342.37
_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_date             2018-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.360(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.8740(5)
_cell_length_b                   4.9000(2)
_cell_length_c                   13.9299(6)
_cell_measurement_reflns_used    5245
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.38
_cell_measurement_theta_min      3.18
_cell_volume                     877.22(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8859
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.987
_diffrn_reflns_theta_min         3.178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1126 before and 0.0664 after correction. The Ratio of minimum to maximum transmission is 0.6955. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1065 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_coef       0.042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0699
_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^)+(0.1120P)^2^+0.6051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.1928
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2799
_reflns_number_total             3178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00487k2.cif
_cod_data_source_block           cu_cxy0340_0m
_cod_database_code               1554358
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.766
_shelx_estimated_absorpt_t_min   0.741
_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 C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(O19) = Uanis(O19A)
3. Others
 Sof(H6B)=Sof(O19A)=Sof(H19A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=
 Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18C)=Sof(H18D)=1-FVAR(1)
 Sof(H6A)=Sof(O19)=Sof(H19)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17A)=
 Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C6(H6A), C6(H6B), C15(H15), C15A(H15A)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C14(H14), C20(H20), C21(H21)
4.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C17A(H17C,H17D)
4.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
4.f Idealised tetrahedral OH refined as rotating group:
 O19(H19), O19A(H19A)
;
_shelx_res_checksum              65613
_shelx_hkl_checksum              19508
_olex2_submission_special_instructions 'No special instructions were received'