Enzymatic Approach to Enantiomerically Pure 5-Alken-2,4-diols and 4-Hydroxy-5-alken-2-ones: Application to the Synthesis of Chiral Synthons
Agnese Abate; Elisabetta Brenna; Alessia Costantini; Claudio Fuganti; Francesco G. Gatti; Luciana Malpezzi; Stefano Serra; Journal of Organic Chemistry 71 (2006) 5228–5240; doi:10.1021/jo060581w

data_4021784
_publ_section_title
;
 Enzymatic Approach to Enantiomerically Pure 5-Alken-2,4-diols and
 4-Hydroxy-5-alken-2-ones: Application to the Synthesis of
 Chiral Synthons
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5228
_journal_page_last               5240
_journal_paper_doi               10.1021/jo060581w
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         C13H18O2
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_chemical_name_systematic        3-methyl-6-phenylhex-5-ene-2,4-diol
_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
_audit_update_record
;
2006-03-16  Received for J. Org. Chem. manuscript jo060581w
            Minor syntax errors corrected (JOC/pH)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4660(10)
_cell_length_b                   9.2700(10)
_cell_length_c                   24.217(3)
_cell_measurement_reflns_used    64
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4
_cell_measurement_theta_min      7.2
_cell_volume                     1227.1(3)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL/NT (Sheldrick, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.1164
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2198
_diffrn_reflns_theta_full        67.48
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         3.65
_diffrn_standards_decay_%        <4%
_diffrn_standards_interval_count 250
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.227
_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   0.5(8)
_refine_ls_extinction_coef       0.0016(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0807
_refine_ls_shift/su_max          0.169
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.5120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1918
_refine_ls_wR_factor_ref         0.2152
_reflns_number_gt                1370
_reflns_number_total             1823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060581wsi20060316_024924.cif
_cod_database_code               4021784