Stereoselective functionalisation of cis- and trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones: asymmetric synthesis of (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids and (2R,3S)-2-amino-2-methyl-3-hydroxy-3-phenylpropanoic acid
Alonso, Francisco; Davies, Stephen G.; Elend, Almut S.; Leech, Michael A.; Roberts, Paul M.; Smith, Andrew D.; Thomson, James E.; Organic & Biomolecular Chemistry 7 (2009) 527–536; doi:10.1039/b814453b

data_7150537
_publ_section_title
;
 Stereoselective functionalisation of cis- and
 trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones:
 asymmetric synthesis of (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids
 and (2R,3S)-2-amino-2-methyl-3-hydroxy-3-phenylpropanoic acid
;
_journal_issue                   3
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              527
_journal_page_last               536
_journal_paper_doi               10.1039/b814453b
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C23 H29 Fe N O3'
_chemical_formula_sum            'C23 H29 Fe N O3'
_chemical_formula_weight         423.3
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             04-11-10
_audit_creation_method           CRYSTALS_ver_12-03-99
_cell_angle_alpha                73.144(3)
_cell_angle_beta                 85.380(3)
_cell_angle_gamma                65.358(3)
_cell_formula_units_Z            2
_cell_length_a                   9.462(1)
_cell_length_b                   10.432(1)
_cell_length_c                   11.673(1)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    100
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1001.21(17)
_computing_cell_refinement
;
USER DEFINED 6
;
_computing_data_collection
;
DATA COLLECTION
;
_computing_data_reduction
;
USER DEFINED 5
;
_computing_molecular_graphics
;
CAMERON (Watkin et al 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al 2001)
;
_computing_structure_solution
;
USER DEFINED 7
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.809
_diffrn_measured_fraction_theta_max 0.785
_diffrn_measurement_device_type
;
Unknown
;
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.04
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3343
_diffrn_reflns_theta_full        21.200
_diffrn_reflns_theta_max         26.751
_diffrn_reflns_theta_min         2.239
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            ' yellow '
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       ' block '
_exptl_crystal_F_000             448.000
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.55
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2799
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000392
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method = Prince modified Chebychev polynomial, (Watkin, 1994)
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

2.12 -0.395 1.76
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0513
_refine_ls_wR_factor_gt          0.0463
_refine_ls_wR_factor_ref         0.0463
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2799
_reflns_number_total             3343
_reflns_threshold_expression     I>4.00u(I)
_cod_data_source_file            b814453b.txt
_cod_data_source_block           CRYSTALS_cif
_cod_original_cell_volume        1001.20837(7)
_cod_database_code               7150537