Double Reformatsky Reaction: Divergent Synthesis of δ-Hydroxy-β-ketoesters
Masahiro Mineno; Yasuhiro Sawai; Kazuaki Kanno; Naotaka Sawada; Hideya Mizufune; Journal of Organic Chemistry 78 (2013) 5843–5850; doi:10.1021/jo400408t

data_4028327
_publ_contact_author_address
;
CMC Center, Takeda Pharmaceutical Company Ltd.,
2-17-85 Jusohonmachi, Yodogawa-ku, Osaka 532-8686, Japan
;
_publ_contact_author_email       masahiro.mineno@takeda.com
_publ_contact_author_fax         +81-6-6300-6251
_publ_contact_author_name        'Masahiro Mineno'
_publ_contact_author_phone       +81-6-6300-6784
_publ_section_title
;
 Double Reformatsky Reaction: Divergent Synthesis of
 \d-Hydroxy-\b-ketoesters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5843
_journal_page_last               5850
_journal_paper_doi               10.1021/jo400408t
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C40 H46 Br2 N2 O10 Zn3'
_chemical_formula_sum            'C40 H46 Br2 N2 O10 Zn3'
_chemical_formula_weight         1070.76
_chemical_name_systematic
;
Ethyl 5-fydroxy-3-oxo-5-phenyl-5-(pyridyn-2-yl)pentanoate zinc complex
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-06-07
_audit_creation_method           'by CrystalStructure 4.0 and SHELXL-97'
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.251(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.6149(3)
_cell_length_b                   14.4589(3)
_cell_length_c                   21.0849(4)
_cell_measurement_reflns_used    70843
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.06
_cell_volume                     4206.4(3)
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2006)'
_computing_data_collection       'RAPID AUTO (Rigaku, 2006)'
_computing_data_reduction        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID 191R'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            77626
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.707
_exptl_absorpt_correction_T_max  0.639
_exptl_absorpt_correction_T_min  0.431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_description       block
_exptl_crystal_F_000             2160.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.620
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         7704
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0234P)^2^+12.2627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                7366
_reflns_number_total             7704
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo400408t_si_002.cif
_cod_data_source_block           zinc_complex_of_3a
_cod_database_code               4028327