Asymmetric Synthesis of α-Amino Acids: Preparation and Alkylation of Monocyclic Iminolactones Derived from α-Methyl trans-Cinnamaldehyde
Ta-Jung Lu; Cheng-Kun Lin; Journal of Organic Chemistry 73 (2008) 9527–9534; doi:10.1021/jo801514g

data_4023922
_publ_section_title
;
 Asymmetric Synthesis of \a-Amino Acids: Preparation and
 Alkylation of Monocyclic Iminolactones Derived from
 \a-Methyl trans-Cinnamaldehyde
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9527
_journal_page_last               9534
_journal_paper_doi               10.1021/jo801514g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                   15.0063(10)
_cell_length_b                   19.0084(14)
_cell_length_c                   6.7002(5)
_cell_measurement_reflns_used    3142
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.887
_cell_measurement_theta_min      2.533
_cell_volume                     1911.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10845
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.064
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.105
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                2387
_reflns_number_total             3762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801514g_si_001.cif
_cod_data_source_block           rxn007m
_cod_database_code               4023922