Synthesis of Trisubstituted Isoxazoles by Palladium(II)-Catalyzed Cascade Cyclization-Alkenylation of 2-Alkyn-1-one O-Methyl Oximes
Zhigang She; Dongyue Niu; Lei Chen; Maria A. Gunawan; Xhesika Shanja; William H. Hersh; Yu Chen; Journal of Organic Chemistry 77 (2012) 3627–3633; doi:10.1021/jo300090k

data_4027112
_publ_contact_author_address
;Department of Chemistry and Biochemistry
Queens College and the Graduate Center of the City University of New York
Flushing, NY 11367-1597
;
_publ_contact_author_email       yu.chen1@qc.cuny.edu
_publ_contact_author_fax         718-997-5531
_publ_contact_author_name        'Yu Chen'
_publ_contact_author_phone       718-997-4132
_publ_section_title
;
 Synthesis of Trisubstituted Isoxazoles by Palladium(II)-Catalyzed Cascade
 Cyclization-Alkenylation of 2-Alkyn-1-one O-Methyl Oximes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3627
_journal_page_last               3633
_journal_paper_doi               10.1021/jo300090k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H19 N O3'
_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38
_chemical_name_common            Naphtho[1,2-c]isoxazole
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 106.4020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.219(4)
_cell_length_b                   6.1210(7)
_cell_length_c                   18.877(2)
_cell_measurement_reflns_used    9781
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.25
_cell_volume                     3460.4(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19036
_diffrn_reflns_theta_full        27.13
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       spar
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00039(19)
_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   1.041
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0481P)^2^+2.3945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                3146
_reflns_number_total             3809
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300090k_si_001.cif
_cod_data_source_block           Naphthoisoxazole_5
_cod_database_code               4027112