Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans.
Deng, Yu-Hua; Chu, Wen-Dao; Zhang, Xiang-Zhi; Yan, Xu; Yu, Ke-Yin; Yang, Liang-Liang; Huang, Hanmin; Fan, Chun-An; The Journal of organic chemistry 82 (2017) 5433–5440; doi:10.1021/acs.joc.7b00370

data_4032531
_publ_section_title
;
 Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of
 Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric
 Synthesis of Functionalized Chromans.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5433
_journal_page_last               5440
_journal_paper_doi               10.1021/acs.joc.7b00370
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H19 Cl O4'
_chemical_formula_sum            'C24 H19 Cl O4'
_chemical_formula_weight         406.84
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-02-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2642(2)
_cell_length_b                   8.2642(2)
_cell_length_c                   59.668(4)
_cell_measurement_reflns_used    1883
_cell_measurement_temperature    294.30(10)
_cell_measurement_theta_max      25.4100
_cell_measurement_theta_min      3.6830
_cell_volume                     4075.1(3)
_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      294.30(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -87.00  -62.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.9280 -178.0000    0.0000 50

  2 omega   -8.00   92.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       25.0530   38.0000 -120.0000 200
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0486322000
_diffrn_orient_matrix_UB_12      -0.0682521000
_diffrn_orient_matrix_UB_13      -0.0025588000
_diffrn_orient_matrix_UB_21      0.0337418000
_diffrn_orient_matrix_UB_22      0.0420582000
_diffrn_orient_matrix_UB_23      -0.0092452000
_diffrn_orient_matrix_UB_31      0.0622017000
_diffrn_orient_matrix_UB_32      0.0305114000
_diffrn_orient_matrix_UB_33      0.0070175000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -73
_diffrn_reflns_number            7842
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75885
_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_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0465P)^2^+0.2939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1365
_reflns_number_gt                3167
_reflns_number_total             4015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00370_si_002.cif
_cod_data_source_block           zhuwd1028
_cod_database_code               4032531
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.069) H3(0.075) H4(0.074) H5(0.066) H7(0.053) H8A(0.059)
 H8B(0.059) H10(0.06) H14(0.076) H15(0.086) H16(0.087) H17(0.076) H19(0.061)
 H20(0.07) H22(0.07) H23(0.085) H24A(0.157) H24B(0.157) H24C(0.157)
 Fixed X: H2(-0.7156) H3(-0.5153) H4(-0.2779) H5(-0.2448) H7(-0.4048) H8A(-
 0.6102) H8B(-0.6563) H10(-0.8934) H14(-1.2234) H15(-1.0398) H16(-0.8091) H17(-
 0.7655) H19(-0.4444) H20(-0.2741) H22(-0.1767) H23(-0.0041) H24A(-1.4213)
 H24B(-1.3314) H24C(-1.4144)
 Fixed Y: H2(0.0462) H3(0.0232) H4(0.1691) H5(0.3389) H7(0.3393) H8A(0.5265)
 H8B(0.5363) H10(0.2037) H14(0.64) H15(0.6132) H16(0.4577) H17(0.3298)
 H19(0.6561) H20(0.876) H22(0.484) H23(0.7012) H24A(0.5857) H24B(0.7107)
 H24C(0.5584)
 Fixed Z: H2(0.0082) H3(-0.0186) H4(-0.0147) H5(0.0157) H7(0.0631) H8A(0.0709)
 H8B(0.0454) H10(0.0755) H14(0.1569) H15(0.1852) H16(0.1802) H17(0.1459)
 H19(0.0221) H20(0.019) H22(0.0722) H23(0.069) H24A(0.1056) H24B(0.1209)
 H24C(0.1316)
;
_olex2_date_sample_data_collection 1414479138.6
_olex2_submission_special_instructions 'No special instructions were received'