Tandem β-Alkylation-α-Arylation of Amines by Carbolithiation and Rearrangement of N-Carbamoyl Enamines (Vinyl Ureas)
Jonathan Clayden; Morgan Donnard; Julien Lefranc; Alberto Minassi; Daniel J. Tetlow; Journal of the American Chemical Society 132 (2010) 6624–6625; doi:10.1021/ja1007992

data_4102399
_publ_section_title
;
 Tandem \b-Alkylation-\a-Arylation of Amines by Carbolithiation and
 Rearrangement of N-Carbamoyl Enamines (Vinyl Ureas)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6624
_journal_page_last               6625
_journal_paper_doi               10.1021/ja1007992
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C21 H31 Cl2 N O'
_chemical_formula_weight         384.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.912(2)
_cell_angle_beta                 94.878(2)
_cell_angle_gamma                94.771(2)
_cell_formula_units_Z            4
_cell_length_a                   8.1672(10)
_cell_length_b                   14.7597(17)
_cell_length_c                   18.591(2)
_cell_measurement_reflns_used    1662
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.9865
_cell_measurement_theta_min      2.291
_cell_volume                     2134.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0616
_diffrn_reflns_av_sigmaI/netI    0.1368
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15451
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0678
_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^)+(0.0802P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1866
_reflns_number_gt                4283
_reflns_number_total             7475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1007992_si_002.cif
_cod_data_source_block           s3320p
_cod_original_cell_volume        2134.0(4)
_cod_database_code               4102399