An Organocatalyzed Enantioselective Synthesis of (2S,3R,4S)-4-Hydroxyisoleucine and Its Stereoisomers
Gullapalli Kumaraswamy; Neerasa Jayaprakash; Balasubramanian Sridhar; Journal of Organic Chemistry 75 (2010) 2745–2747; doi:10.1021/jo100233u

data_4025365
_publ_contact_author_address
;Laboratory of X-ray Crystallography
Indian Institute of Chemical Technology
Hyderbad - 500 607
India.
;
_publ_contact_author_email       sshiya@yahoo.com
_publ_contact_author_fax         91-40-27193118
_publ_contact_author_name        'Sridhar, B'
_publ_contact_author_phone       91-40-27193118
_publ_section_title
;
 An Organocatalyzed Enantioselective Synthesis of
 (2S,3R,4S)-4-Hydroxyisoleucine and Its Stereoisomers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2745
_journal_page_last               2747
_journal_paper_doi               10.1021/jo100233u
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H23 N O4'
_chemical_formula_sum            'C14 H23 N O4'
_chemical_formula_weight         269.33
_chemical_name_systematic
'tert-butyl(1S, 2S, 3R)-1-(furan-2-yl)-3-hydroxy-2-methylbutylcarbamate'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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                 94.436(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.363(3)
_cell_length_b                   9.031(4)
_cell_length_c                   13.892(6)
_cell_measurement_reflns_used    1166
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.59
_cell_measurement_theta_min      2.69
_cell_volume                     795.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4672
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.69
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1487
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0501P)^2^+0.0016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                1163
_reflns_number_total             1487
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo100233u_si_001.cif
_cod_data_source_block           ag69m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025365