Fast Pd- and Pd/Cu-Catalyzed Direct C-H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters
Emilien Demory; Daniel Farran; Benoit Baptiste; Pierre Y. Chavant; Véronique Blandin; Journal of Organic Chemistry 77 (2012) 7901–7912; doi:10.1021/jo301114k

data_4027499
_publ_contact_author_name
;
;
_publ_section_title
;
 Fast Pd- and Pd/Cu-Catalyzed Direct C-H Arylation of Cyclic Nitrones.
 Application to the Synthesis of Enantiopure Quaternary \a-Amino Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7901
_journal_page_last               7912
_journal_paper_doi               10.1021/jo301114k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_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_creation_date             2012-03-07
_audit_creation_method
;
  Olex2 1.1
  (compiled Sep 28 2011 20:36:17, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.07(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.988(2)
_cell_length_b                   7.3613(15)
_cell_length_c                   20.055(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.36
_cell_measurement_theta_min      17.85
_cell_volume                     1447.1(5)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      296
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_detector_type            'scintillation LiI'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker-Enraf-Nonius MACH3'
_diffrn_measurement_method       'non-profiled \w/2\t scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.083779
_diffrn_orient_matrix_UB_12      -0.017666
_diffrn_orient_matrix_UB_13      0.035713
_diffrn_orient_matrix_UB_21      -0.054206
_diffrn_orient_matrix_UB_22      0.024550
_diffrn_orient_matrix_UB_23      0.036089
_diffrn_orient_matrix_UB_31      -0.021228
_diffrn_orient_matrix_UB_32      -0.132435
_diffrn_orient_matrix_UB_33      0.001900
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2827
_diffrn_reflns_theta_full        72.90
_diffrn_reflns_theta_max         72.90
_diffrn_reflns_theta_min         4.49
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Cu
_diffrn_source_type              'fine-focus sealed tube'
_diffrn_standards_decay_%        8
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0101(15)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1313P)^2^+0.3893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.1932
_reflns_number_gt                2132
_reflns_number_total             2753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301114k_si_003.cif
_cod_data_source_block           chav15
_cod_database_code               4027499
_diffrn_standards_decay_corr_max 1.007
_diffrn_standards_decay_corr_min 0.831