Indium(III)-catalyzed asymmetric hetero-Diels-Alder reaction of Brassard-type diene with aliphatic aldehydes.
Lin, Lili; Kuang, Yulong; Liu, Xiaohua; Feng, Xiaoming; Organic letters 13 (2011) 3868–3871; doi:10.1021/ol2013999

data_1502293
_publ_section_title
;
 Indium(III)-catalyzed asymmetric hetero-Diels-Alder reaction of
 Brassard-type diene with aliphatic aldehydes.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3868
_journal_page_last               3871
_journal_paper_doi               10.1021/ol2013999
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H20 O3'
_chemical_formula_sum            'C13 H20 O3'
_chemical_formula_weight         224.29
_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                 94.844(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.1581(12)
_cell_length_b                   9.443(2)
_cell_length_c                   12.776(3)
_cell_measurement_reflns_used    6240
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.47
_cell_volume                     620.1(2)
_computing_cell_refinement       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_collection       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_reduction        'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     1.54186
_diffrn_reflns_av_R_equivalents  0.1423
_diffrn_reflns_av_sigmaI/netI    0.1812
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7045
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.9355
_exptl_absorpt_correction_T_min  0.6493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi March, 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.050
_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       0.015(3)
_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   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                1329
_reflns_number_total             2142
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2013999_si_001.cif
_cod_data_source_block           sx2949
_cod_original_cell_volume        620.1(3)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1502293