Diastereoselective Rhodium-Catalyzed Ene-Cycloisomerization Reactions of Alkenylidenecyclopropanes: Total Synthesis of (-)-α-Kainic Acid
P. Andrew Evans; Phillip A. Inglesby; Journal of the American Chemical Society 134 (2012) 3635–3638; doi:10.1021/ja210804r

data_4117556
_publ_section_title
;
 Diastereoselective Rhodium-Catalyzed Ene-Cycloisomerization Reactions of
 Alkenylidenecyclopropanes: Total Synthesis of (-)-\a-Kainic Acid
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3635
_journal_page_last               3638
_journal_paper_doi               10.1021/ja210804r
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C23 H27 Cl2 N5 O6 S'
_chemical_formula_weight         572.47
_chemical_name_common            PIIV48work
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.918(4)
_cell_angle_beta                 96.052(3)
_cell_angle_gamma                92.312(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2277(17)
_cell_length_b                   9.7367(18)
_cell_length_c                   15.016(3)
_cell_measurement_reflns_used    11553
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      0.97
_cell_volume                     1293.2(4)
_computing_cell_refinement       'SAINT v6.45a (Bruker, 2005)'
_computing_data_collection       'SMART v.5.632 (Bruker, 2005)'
_computing_data_reduction        'SAINT v6.45a (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX detector'
_diffrn_measurement_method       '\w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7623
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_T_max  0.9381
_exptl_absorpt_correction_T_min  0.8688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008-1 (Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5499
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+1.4456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                4992
_reflns_number_total             5499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja210804r_si_001.cif
_cod_data_source_block
Z:\DEPT\EVANS\PINGLESBY\PIIV48\PIIV48work\piiv481m.CIF
_cod_database_code               4117556