One-Pot Synthesis of Indolizines via Sequential Rhodium-Catalyzed [2 + 1]-Cyclopropanation, Palladium-Catalyzed Ring Expansion, and Oxidation Reactions from Pyridotriazoles and 1,3-Dienes.
Kim, Hyunseok; Kim, Sanghyuck; Kim, Jiyeon; Son, Jeong-Yu; Baek, Yonghyeon; Um, Kyusik; Lee, Phil Ho; Organic letters 19 (2017) 5677–5680; doi:10.1021/acs.orglett.7b02826

data_1547640
_publ_section_title
;
 One-Pot Synthesis of Indolizines via Sequential Rhodium-Catalyzed [2 +
 1]-Cyclopropanation, Palladium-Catalyzed Ring Expansion, and Oxidation
 Reactions from Pyridotriazoles and 1,3-Dienes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5677
_journal_page_last               5680
_journal_paper_doi               10.1021/acs.orglett.7b02826
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C22 H21 N O4'
_chemical_formula_weight         363.40
_chemical_name_common            KSH-2428
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                100.040(2)
_cell_angle_beta                 92.095(2)
_cell_angle_gamma                110.687(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8929(3)
_cell_length_b                   7.6318(3)
_cell_length_c                   19.0999(9)
_cell_measurement_reflns_used    8318
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      27.7419
_cell_measurement_theta_min      2.8975
_cell_volume                     920.31(7)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29961
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1012P)^2^+0.1748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1780
_reflns_number_gt                3275
_reflns_number_total             4712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02826_si_003.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 1547640--1547641.cif.'
_cod_database_code               1547640