Amidopalladation of Alkoxyallenes Applied in the Synthesis of an Enantiopure 1-Ethylquinolizidine Frog Alkaloid
Sape S. Kinderman; René de Gelder; Jan H. van Maarseveen; Hans E. Schoemaker; Henk Hiemstra; Floris P. J. T. Rutjes; Journal of the American Chemical Society 126 (2004) 4100–4101; doi:10.1021/ja039919j

data_4112400
_publ_contact_author
;
     Prof.dr. F.P.J.T. Rutjes
     Department of Organic Chemistry
     NSRIM Institute               
     University of Nijmegen
     Toernooiveld 1
     6525 ED  Nijmegen
     The Netherlands
;
_publ_contact_author_email       rutjes@sci.kun.nl
_publ_contact_author_fax         '031 024 3553450'
_publ_contact_author_phone       '031 024 3653202'
_publ_section_title
;
 Amidopalladation of Alkoxyallenes Applied in the Synthesis of an
 Enantiopure 1-Ethylquinolizidine Frog Alkaloid
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4100
_journal_page_last               4101
_journal_paper_doi               10.1021/ja039919j
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.28
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2bc 2'
_symmetry_space_group_name_H-M   'P 2 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2003-09-08
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7451(5)
_cell_length_b                   10.4763(6)
_cell_length_c                   15.3434(6)
_cell_measurement_reflns_used    11097
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.500
_cell_measurement_theta_min      3.530
_cell_volume                     1244.96(12)
_computing_data_collection       'Nonius "EvalCCD" program suite'
_computing_data_reduction        'Nonius "EvalCCD" program suite'
_computing_molecular_graphics
;
PLUTON (Spek, 1993),
PLATON (Spek, 1990, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
CRUNCH (de Gelder et al., 1993),
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 18.4
_diffrn_measurement_device       'Nonius KappaCCD on rotating anode'
_diffrn_measurement_method       'area detector \f and \w scan'
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11097
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.53
_diffrn_standards_decay_%        0.000
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'colorless transparant'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       regular
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_Flack   0.3(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.058
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0442
_refine_ls_R_factor_obs          0.0442
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.0548P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0813
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_obs         0.0730
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                1927
_reflns_number_observed          1927
_reflns_number_total             2783
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja039919jsi20031203_065627.cif
_cod_data_source_block           SK551
_cod_database_code               4112400