Highly regio- and stereoselective (3 + 2) annulation reaction of allenoates with 3-methyleneindolin-2-ones catalyzed by a planar chiral [2.2]paracyclophane-based bifunctional phosphine-phenol catalyst.
Kitagaki, Shinji; Nakayoshi, Tomoki; Masunaka, Sota; Uchida, Akane; Inano, Mai; Yoshida, Emika; Washino, Yusuke; Aoyama, Hiroshi; Yoshida, Keisuke; Organic & biomolecular chemistry 22 (2024) 7817–7833; doi:10.1039/d4ob00831f

data_7160053
_publ_section_title
;
 Highly regio- and stereoselective (3 + 2) annulation reaction of
 allenoates with 3-methyleneindolin-2-ones catalyzed by a planar chiral
 [2.2]paracyclophane-based bifunctional phosphine-phenol catalyst.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7817
_journal_page_last               7833
_journal_paper_doi               10.1039/d4ob00831f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H21 N O4'
_chemical_formula_sum            'C23 H21 N O4'
_chemical_formula_weight         375.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-03-28 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                88.347(6)
_cell_angle_beta                 69.418(5)
_cell_angle_gamma                88.399(6)
_cell_formula_units_Z            8
_cell_length_a                   13.0103(8)
_cell_length_b                   17.3840(11)
_cell_length_c                   17.8554(11)
_cell_measurement_reflns_used    31385
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.67
_cell_measurement_theta_min      3.63
_cell_volume                     3778.3(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            42483
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         3.630
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.802
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            colorless
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_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584.00
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.83
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         13547
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.1191
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1773P)^2^+20.0224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3659
_refine_ls_wR_factor_ref         0.3774
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10548
_reflns_number_total             13547
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d4ob00831f3.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7160051--7160053.cif.'
_cod_original_cell_volume        3778.4(4)
_cod_database_code               7160053
_shelx_res_checksum              3329