Rhodium-catalyzed olefin isomerization/enantioselective intramolecular Alder-ene reaction cascade.
Okamoto, Ryuichi; Okazaki, Eri; Noguchi, Keiichi; Tanaka, Ken; Organic letters 13 (2011) 4894–4897; doi:10.1021/ol201986e

data_1502453
_publ_section_title
;
 Rhodium-catalyzed olefin isomerization/enantioselective intramolecular
 Alder-ene reaction cascade.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4894
_journal_page_last               4897
_journal_paper_doi               10.1021/ol201986e
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H17 Br O'
_chemical_formula_sum            'C22 H17 Br O'
_chemical_formula_weight         377.27
_chemical_name_systematic
;
 (S)-(-)-1-(4-Bromobenzylidene)-2-isopropenyl-1,2-
 dihydronaphtho[2,1-b]furan [(S)-(-)-3k]
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.64430(10)
_cell_length_b                   8.8426(2)
_cell_length_c                   33.8277(6)
_cell_measurement_reflns_used    28821
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.92
_cell_volume                     1688.35(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2009)'
_computing_data_reduction        'RAPID AUTO'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            29394
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         5.17
_exptl_absorpt_coefficient_mu    3.341
_exptl_absorpt_correction_T_max  0.716
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881  1256 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.024(12)
_refine_ls_extinction_coef       0.00296(17)
_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   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+0.1471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0509
_reflns_number_gt                3037
_reflns_number_total             3095
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201986e_si_001.cif
_cod_data_source_block           I
_cod_database_code               1502453