Direct Bis-Arylation of Cyclobutanecarboxamide via Double C-H Activation: An Auxiliary-Aided Diastereoselective Pd-Catalyzed Access to Trisubstituted Cyclobutane Scaffolds Having Three Contiguous Stereocenters and an All-cis Stereochemistry
Ramarao Parella; Bojan Gopalakrishnan; Srinivasarao Arulananda Babu; Journal of Organic Chemistry 78 (2013) 11911–11934; doi:10.1021/jo4019733

data_4028807
_publ_contact_author_address
;
Department of Chemical Sciences
Indian Institute of Science Education and Research, Mohali, Sector 81,
S. A. S. Nagar, Manauli PO, Punjab, INDIA. 140306.
;
_publ_contact_author_email       sababu@iisermohali.ac.in
_publ_contact_author_fax         '0091 (172) 2240266'
_publ_contact_author_name        'Babu, S. A.'
_publ_contact_author_phone       '0091 (172) 2240124'
_publ_section_title
;
 Direct Bis-Arylation of Cyclobutanecarboxamide via Double C-H Activation:
 An Auxiliary-Aided Diastereoselective Pd-Catalyzed Access to
 Trisubstituted Cyclobutane Scaffolds Having Three Contiguous
 Stereocenters and an All-cis Stereochemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11911
_journal_page_last               11934
_journal_paper_doi               10.1021/jo4019733
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C26 H20 N4 O5'
_chemical_formula_sum            'C26 H20 N4 O5'
_chemical_formula_weight         468.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-01-11T11:28:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.233(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.718(3)
_cell_length_b                   14.078(3)
_cell_length_c                   13.761(3)
_cell_measurement_reflns_used    3291
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.392
_cell_measurement_theta_min      2.778
_cell_volume                     2263.9(9)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16173
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.07
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.6791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0531 before and 0.0455 after correction.
        The Ratio of minimum to maximum transmission is 0.9103.
        The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0060(9)
_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   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.3913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                2735
_reflns_number_total             3998
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4019733_si_004.cif
_cod_data_source_block           sci104_0m
_cod_original_cell_volume        2264.0(8)
_cod_database_code               4028807