Asymmetric Diels-Alder reaction of 3-olefinic benzofuran-2-ones and polyenals: construction of chiral spirocyclic benzofuran-2-ones.
Li, Xin; Lin, Mao-Hui; Han, Yu; Wang, Feng; Cheng, Jin-Pei; Organic letters 16 (2014) 114–117; doi:10.1021/ol403094a

data_1513548
_publ_section_title
;
 Asymmetric Diels-Alder reaction of 3-olefinic benzofuran-2-ones and
 polyenals: construction of chiral spirocyclic benzofuran-2-ones.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              114
_journal_page_last               117
_journal_paper_doi               10.1021/ol403094a
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H18 O5'
_chemical_formula_weight         314.32
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6305(19)
_cell_length_b                   11.802(2)
_cell_length_c                   13.800(3)
_cell_measurement_reflns_used    16125
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.93
_cell_volume                     1568.5(5)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16125
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         4.93
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.5658
_exptl_absorpt_correction_T_min  0.5658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T. Higashi, March, 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.80
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0236(9)
_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   1.215
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0173P)^2^+0.8898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                2726
_reflns_number_total             2812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403094a_si_001.cif
_cod_data_source_block           a
_cod_original_cell_volume        1568.4(5)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1513548