A Domino Michael/Dieckmann Process as an Entry to α-(Hydroxymethyl)glutamic Acid
Carlos Aydillo; Gonzalo Jiménez-Osés; Alberto Avenoza; Jesús H. Busto; Jesús M. Peregrina; María M. Zurbano; Journal of Organic Chemistry 76 (2011) 6990–6996; doi:10.1021/jo201067n

data_4026559
_publ_section_title
;
 A Domino Michael/Dieckmann Process as an Entry to
 \a-(Hydroxymethyl)glutamic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6990
_journal_page_last               6996
_journal_paper_doi               10.1021/jo201067n
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H17 N O7'
_chemical_formula_sum            'C14 H17 N O7'
_chemical_formula_weight         311.29
_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                 119.333(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7926(5)
_cell_length_b                   8.9256(3)
_cell_length_c                   14.0637(4)
_cell_measurement_reflns_used    14759
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1509.36(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6368
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         4.03
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.163
_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   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0522P)^2^+0.1405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                2388
_reflns_number_total             3616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201067n_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1509.37(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026559