Synthesis of a-fluoro-B-hydroxy esters by an enantioselective Reformatsky-type reaction
Michal Fornalczyk; Kuldip Singh; Alison M. Stuart; Chem.Commun. 48 (2012) 3500–; doi:10.1039/c2cc17985g

data_7107514
_publ_section_title
;
 Synthesis of a-fluoro-B-hydroxy esters by an enantioselective
 Reformatsky-type reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              3500
_journal_paper_doi               10.1039/c2cc17985g
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ,rm
_chemical_formula_moiety         'C18 H20 F N O2'
_chemical_formula_sum            'C18 H20 F N O2'
_chemical_formula_weight         301.35
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 109.351(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.119(6)
_cell_length_b                   5.5114(16)
_cell_length_c                   15.207(4)
_cell_measurement_reflns_used    337
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.306
_cell_measurement_theta_min      2.234
_cell_volume                     1511.9(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1603
_diffrn_reflns_av_sigmaI/netI    0.1853
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5986
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction based on 1017 reflections(SADABS);Rint 0.0890 before
correction and 0.0545 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         1648
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0172P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                856
_reflns_number_total             1648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc17985g.txt
_cod_data_source_block           10097
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7107514