Lewis-Base-Catalyzed Asymmetric [3 + 3] Annulation Reaction of Morita–Baylis–Hillman Carbonates: Enantioselective Synthesis of Spirocyclohexenes
Yang, Wenjun; Sun, Wei; Zhang, Cheng; Wang, Qijun; Guo, Zhenyan; Mao, Biming; Liao, Jianning; Guo, Hongchao; ACS Catalysis 7 (2017) 3142–; doi:10.1021/acscatal.7b00320

data_4514140
_publ_section_title
;
 Lewis-Base-Catalyzed Asymmetric [3 + 3] Annulation Reaction of
 Morita--Baylis--Hillman Carbonates: Enantioselective Synthesis of
 Spirocyclohexenes
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              3142
_journal_paper_doi               10.1021/acscatal.7b00320
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H30 F6 N2 O4'
_chemical_formula_sum            'C42 H30 F6 N2 O4'
_chemical_formula_weight         740.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-21
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8643(8)
_cell_length_b                   17.5771(8)
_cell_length_c                   22.5359(8)
_cell_measurement_reflns_used    5755
_cell_measurement_temperature    106.3
_cell_measurement_theta_max      70.9605
_cell_measurement_theta_min      3.9188
_cell_volume                     3511.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      106.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega   34.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   15.0000 -120.0000 27

  2 omega  -46.00    9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   15.0000 -120.0000 55

  3 omega  -32.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -150.0000 81

  4 omega   55.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -140.0000   30.0000 42

  5 omega   20.00   51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000 -180.0000 31

  6 omega  -26.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -60.0000  -37.0000 79

  7 omega   40.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 53

  8 omega   40.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

  9 omega   93.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   60.0000   41.0000 81

 10 omega   41.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 28

 11 omega   63.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 26

 12 omega   86.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 90

 13 omega   44.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 59

 14 omega   94.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  150.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1045941000
_diffrn_orient_matrix_UB_12      0.0435093000
_diffrn_orient_matrix_UB_13      -0.0428062000
_diffrn_orient_matrix_UB_21      0.0655296000
_diffrn_orient_matrix_UB_22      -0.0759103000
_diffrn_orient_matrix_UB_23      -0.0223658000
_diffrn_orient_matrix_UB_31      -0.1223017000
_diffrn_orient_matrix_UB_32      -0.0034216000
_diffrn_orient_matrix_UB_33      -0.0483773000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12075
_diffrn_reflns_theta_full        71.31
_diffrn_reflns_theta_max         71.31
_diffrn_reflns_theta_min         3.92
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.12(10)
_refine_ls_extinction_coef       0.00167(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0438P)^2^+0.9345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                6335
_reflns_number_total             6647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs7b00320_si_003.cif
_cod_data_source_block           exp_4656
_cod_database_code               4514140
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97