Multifunctional chiral phosphine-catalyzed [3+2] annulation of Morita-Baylis-Hillman carbonates with cyclopentenones: asymmetric synthesis of 4-oxo-hexahydropentalenes.
Wang, Chang; Gao, Zhenzhen; Zhou, Leijie; Wang, Qijun; Wu, Yang; Yuan, Chunhao; Liao, Jianning; Xiao, Yumei; Guo, Hongchao; Chemical communications (Cambridge, England) 54 (2018) 279–282; doi:10.1039/c7cc08380g

data_7120949
_publ_section_title
;
 Multifunctional chiral phosphine-catalyzed [3+2] annulation of
 Morita-Baylis-Hillman carbonates with cyclopentenones: asymmetric
 synthesis of 4-oxo-hexahydropentalenes.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              279
_journal_page_last               282
_journal_paper_doi               10.1039/c7cc08380g
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 O3'
_chemical_formula_sum            'C23 H20 O3'
_chemical_formula_weight         344.39
_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_date             2017-04-11
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2017-09-12 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.490(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2479(5)
_cell_length_b                   10.4410(5)
_cell_length_c                   9.4838(5)
_cell_measurement_reflns_used    3502
_cell_measurement_temperature    109.1
_cell_measurement_theta_max      71.0850
_cell_measurement_theta_min      4.2308
_cell_volume                     903.20(8)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      109.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -30.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000   60.0000 26

  2 omega  -32.00   42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   90.0000 74

  3 omega   12.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -60.0000 86

  4 omega  -25.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000    0.0000 81

  5 omega   38.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -105.0000  109.0000 33

  6 omega  -10.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  -30.0000 71

  7 omega   30.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -105.0000  -70.0000 49

  8 omega   10.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -120.0000 88

  9 omega  100.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 26

 10 omega  132.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 39

 11 omega   59.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 37

 12 omega   42.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 55

 13 omega   86.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 86

 14 omega   44.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 44

 15 omega  101.00  153.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 52

 16 omega   91.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 32

 17 omega   87.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -105.0000  150.0000 26

 18 omega   42.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 56

 19 omega   38.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -105.0000  150.0000 45

 20 omega  101.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 71

 21 omega   99.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 68

 22 omega   43.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 55

 23 omega   73.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 67

 24 omega   63.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -114.0000  -59.0000 48

 25 omega   61.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -105.0000  109.0000 35

 26 omega   81.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -107.0000   -1.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0752920000
_diffrn_orient_matrix_UB_12      0.1315583000
_diffrn_orient_matrix_UB_13      -0.0240955000
_diffrn_orient_matrix_UB_21      -0.1373589000
_diffrn_orient_matrix_UB_22      -0.0546370000
_diffrn_orient_matrix_UB_23      0.0508159000
_diffrn_orient_matrix_UB_31      0.0627567000
_diffrn_orient_matrix_UB_32      0.0384710000
_diffrn_orient_matrix_UB_33      0.1549146000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5793
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.224
_diffrn_reflns_theta_min         4.727
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91732
_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_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0490P)^2^+0.1197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3340
_reflns_number_total             3387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08380g2.cif
_cod_data_source_block           exp_4881
_cod_depositor_comments
'Adding full bibliography for 7120949--7120950.cif.'
_cod_database_code               7120949
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.801
_shelx_estimated_absorpt_t_min   0.755
_shelx_res_checksum              79511
_shelx_shelxl_version_number     2014/7