Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives
Norihiro Ikemoto; David M. Tellers; Spencer D. Dreher; Jinchu Liu; Angie Huang; Nelo R. Rivera; Eugenia Njolito; Yi Hsiao; J. Christopher McWilliams; J. Michael Williams; Joseph D. Armstrong; Yongkui Sun; David J. Mathre; Edward J. J. Grabowski; Richard D. Tillyer; Journal of the American Chemical Society 126 (2004) 3048–3049; doi:10.1021/ja038812t

data_4112309
_publ_contact_author             'Nori Ikemoto'
_publ_contact_author_email       norihiro_ikemoto@merck.com
_publ_section_title
;
 Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of
 Enamines for the Synthesis of Chiral \b-Amino Acid Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3048
_journal_page_last               3049
_journal_paper_doi               10.1021/ja038812t
_journal_volume                  126
_journal_year                    2004
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H20 N2 O3'
_chemical_formula_sum            'C15 H20 N2 O3'
_chemical_formula_weight         276.33
_chemical_melting_point          435
_chemical_name_common            DJM2471m
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.946(4)
_cell_length_b                   10.000(4)
_cell_length_c                   16.443(7)
_cell_measurement_reflns_used    7734
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.38
_cell_volume                     1471.0(11)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15694
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      0
_exptl_crystal_description       rod
_exptl_crystal_F_000             592
_exptl_crystal_preparation       methanol
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_coef       0.023(4)
_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   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.0097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                2815
_reflns_number_total             3035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja038812tsi20030930_051909.cif
_cod_data_source_block           djm2471m
_cod_database_code               4112309