Preparation of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation and Hydrozincation of Ynamides
Benoit Gourdet; Mairi E. Rudkin; Ciorsdaidh A. Watts; Hon Wai Lam; Journal of Organic Chemistry 74 (2009) 7849–7858; doi:10.1021/jo901658v

data_4024922
_publ_contact_author_email       f.j.white@sms.ed.ac.uk
_publ_contact_author_name        'Fraser J. White'
_publ_section_title
;
Preparation of Multisubstituted Enamides via Rhodium-Catalyzed
Carbozincation and Hydrozincation of Ynamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7849
_journal_page_last               7858
_journal_paper_doi               10.1021/jo901658v
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'Ciorsdaidh Watts'
_chemical_formula_moiety         'C20 H21 N O3'
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_weight         323.38
_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                89.578(2)
_cell_angle_beta                 67.590(2)
_cell_angle_gamma                69.602(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6153(4)
_cell_length_b                   9.6328(4)
_cell_length_c                   10.1230(4)
_cell_measurement_reflns_used    5211
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.28
_cell_volume                     803.88(6)
_computing_cell_refinement       Saint
_computing_data_reduction        Saint
_computing_molecular_graphics    Shelxp
_computing_publication_material  'Platon, encifer'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxs Sheldrick'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9584
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.8651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_recrystallization_method
'Diffusion od hexane into EtOac Solution'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0613P)^2^+0.2051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                3025
_reflns_number_total             3278
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901658v_si_002.cif
_cod_data_source_block           hl9002
_cod_database_code               4024922