Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates.
Xu, Xinfang; Shabashov, Dmitry; Zavalij, Peter Y.; Doyle, Michael P.; Organic letters 14 (2012) 800–803; doi:10.1021/ol203331r

data_1503593
_publ_section_title
;
 Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with
 Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              800
_journal_page_last               803
_journal_paper_doi               10.1021/ol203331r
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H17 N O4'
_chemical_formula_sum            'C15 H17 N O4'
_chemical_formula_weight         275.30
_chemical_name_common            Organic
_chemical_name_systematic
;
Organic
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 104.6258(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8866(8)
_cell_length_b                   15.5331(10)
_cell_length_c                   7.5540(5)
_cell_measurement_reflns_used    9195
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.9
_cell_measurement_theta_min      2.2
_cell_volume                     1349.54(15)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 11.198
_diffrn_detector_type            'Bruker Smart Apex2, CCD'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      610,610,610,1200
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0488669
_diffrn_orient_matrix_UB_12      -0.0597582
_diffrn_orient_matrix_UB_13      -0.0008531
_diffrn_orient_matrix_UB_21      -0.0435121
_diffrn_orient_matrix_UB_22      -0.0010853
_diffrn_orient_matrix_UB_23      -0.0867282
_diffrn_orient_matrix_UB_31      0.1201511
_diffrn_orient_matrix_UB_32      0.0239213
_diffrn_orient_matrix_UB_33      -0.0060633
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15448
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0407
_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^)+(0.01P)^2^+1.46P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                2171
_reflns_number_total             2374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203331r_si_001.cif
_cod_data_source_block           2185
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1503593