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_4026561
_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         'C13 H17 N O7'
_chemical_formula_sum            'C13 H17 N O7'
_chemical_formula_weight         299.28
_chemical_name_common            c450-2
_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                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   7.2387(3)
_cell_length_b                   8.1145(4)
_cell_length_c                   23.7050(10)
_cell_measurement_reflns_used    12534
_cell_measurement_temperature    120(2)
_cell_volume                     1392.39(11)
_computing_cell_refinement       'Denzo and Scalepak (1997)'
_computing_data_collection       'Nonius Kappa CCD'
_computing_data_reduction        'Denzo and Scalepak (1997)'
_computing_molecular_graphics    'ORTEP III'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11213
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.82
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0470P)^2^+0.3253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                2671
_reflns_number_total             3129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201067n_si_003.cif
_cod_data_source_block           rxc450
_cod_database_code               4026561