Pd-catalyzed C4-olefination of oxazoles via C-H bond activation: divergent synthesis of functionalized amino alcohol and amino acid derivatives.
Cui, Sunliang; Wojtas, Lukasz; Antilla, Jon C.; Organic letters 13 (2011) 5040–5043; doi:10.1021/ol201865h

data_1502417
_publ_section_title
;
 Pd-catalyzed C4-olefination of oxazoles via C-H bond activation:
 divergent synthesis of functionalized amino alcohol and amino acid
 derivatives.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5040
_journal_page_last               5043
_journal_paper_doi               10.1021/ol201865h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C16 H23 N O5'
_chemical_formula_sum            'C16 H23 N O5'
_chemical_formula_weight         309.35
_chemical_name_systematic
;
ethyl 5-methoxy-4-(4-methoxybenzamido)pentanoate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 100.896(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7468(5)
_cell_length_b                   5.0698(2)
_cell_length_c                   21.3719(7)
_cell_measurement_reflns_used    2403
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.2
_cell_measurement_theta_min      4.2
_cell_volume                     1569.03(10)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5840
_diffrn_reflns_theta_full        66.13
_diffrn_reflns_theta_max         66.13
_diffrn_reflns_theta_min         4.21
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1196 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.04(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0425P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                2382
_reflns_number_total             2543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201865h_si_002.cif
_cod_data_source_block           4b
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               1502417