New asymmetric synthesis of protein farnesyltransferase inhibitors via palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles
Kerhervé, Jennifer; Botuha, Candice; Dubois, Joëlle; Organic & Biomolecular Chemistry 7 (2009) 2214–2222; doi:10.1039/b902601k

data_7150659
_publ_section_title
;
 New asymmetric synthesis of protein farnesyltransferase inhibitors via
 palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles
;
_journal_issue                   10
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2214
_journal_page_last               2222
_journal_paper_doi               10.1039/b902601k
_journal_volume                  7
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H23 N O5'
_chemical_formula_sum            'C19 H23 N O5'
_chemical_formula_weight         345.38
_chemical_name_systematic
;
(R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 106.652(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.361(3)
_cell_length_b                   10.817(4)
_cell_length_c                   12.310(4)
_cell_measurement_reflns_used    1596
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      0.41
_cell_volume                     939.1(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8153
_diffrn_reflns_theta_full        24.59
_diffrn_reflns_theta_max         24.59
_diffrn_reflns_theta_min         2.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.070(12)
_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   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0506P)^2^+0.1088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                1334
_reflns_number_total             1648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b902601k.txt
_cod_data_source_block           jz363
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7150659