Aminocatalytic Asymmetric exo-Diels-Alder Reaction with Methiodide Salts of Mannich Bases and 2,4-Dienals to Construct Chiral Spirocycles.
Zhang, Shan-Jun; Zhang, Jun; Zhou, Qing-Qing; Dong, Lin; Chen, Ying-Chun; Organic letters 15 (2013) 968–971; doi:10.1021/ol4002015

data_1508964
_publ_section_title
;
 Aminocatalytic Asymmetric exo-Diels-Alder Reaction with Methiodide Salts
 of Mannich Bases and 2,4-Dienals to Construct Chiral Spirocycles.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              968
_journal_page_last               971
_journal_paper_doi               10.1021/ol4002015
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H24 O4'
_chemical_formula_weight         388.44
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 103.2230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.47420(10)
_cell_length_b                   11.5299(2)
_cell_length_c                   10.62130(10)
_cell_measurement_reflns_used    6923
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.7382
_cell_measurement_theta_min      3.8306
_cell_volume                     1010.26(2)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8746
_diffrn_reflns_theta_full        65.08
_diffrn_reflns_theta_max         65.08
_diffrn_reflns_theta_min         7.60
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.8097
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0500P)^2^+0.2346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                3376
_reflns_number_total             3388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4002015_si_002.cif
_cod_data_source_block           10a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1508964