Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones
Wang, De; Wang, Guo-Peng; Sun, Yao-Liang; Zhu, Shou-Fei; Wei, Yin; Zhou, Qi-Lin; Shi, Min; Chem. Sci. 6 (2015) 7319–; doi:10.1039/C5SC03135D

data_1531046
_publ_section_title
;
 Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates
 with benzofuranone-derived olefins for a highly regio-, diastereo- and
 enantioselective synthesis of spiro-benzofuranones
;
_journal_issue                   12
_journal_name_full               'Chem. Sci.'
_journal_page_first              7319
_journal_paper_doi               10.1039/C5SC03135D
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46
_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_method           SHELXL-2014
_audit_update_record
;
2014-06-26 deposited with the CCDC.
2015-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.16260(10)
_cell_length_b                   12.2302(2)
_cell_length_c                   11.07420(10)
_cell_measurement_reflns_used    6378
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      68.94
_cell_measurement_theta_min      4.07
_cell_volume                     1083.72(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7473
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.357
_diffrn_reflns_theta_min         4.072
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 1193 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.13(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.1082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.580
_reflns_Friedel_fraction_full    0.645
_reflns_Friedel_fraction_max     0.629
_reflns_number_gt                3271
_reflns_number_total             3297
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc03135d2.cif
_cod_data_source_block           cu_dm14382_0m
_cod_depositor_comments
'Adding full bibliography for 1531044--1531046.cif.'
_cod_database_code               1531046
_shelx_estimated_absorpt_t_min   0.838
_shelx_estimated_absorpt_t_max   0.883
_shelxl_version_number           2014-3
_shelx_res_checksum              62732
_shelx_hkl_checksum              61153