Stereoselective pinacol coupling of chiral formylferrocene using divalent samarium triflate: preparation of a new chiral bisferrocenyl oxazoline ligand and its application to asymmetric Diels-Alder reactions.
Fukuzawa, Shin-ichi; Yahara, Yuusuke; Kamiyama, Akira; Hara, Masumi; Kikuchi, Satoshi; Organic letters 7 (2005) 5809–5812; doi:10.1021/ol0523291

data_1506766
_publ_section_title
;
 Stereoselective pinacol coupling of chiral formylferrocene using divalent
 samarium triflate: preparation of a new chiral bisferrocenyl oxazoline
 ligand and its application to asymmetric Diels-Alder reactions.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              5809
_journal_page_last               5812
_journal_paper_doi               10.1021/ol0523291
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C34 H40 Fe2 N2 O4 '
_chemical_formula_sum            'C34 H40 Fe2 N2 O4'
_chemical_formula_weight         652.39
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.686(4)
_cell_length_b                   23.733(9)
_cell_length_c                   25.310(9)
_cell_measurement_reflns_used    13139
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     5818(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure Ver. 3.5.1'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.9751
_diffrn_measured_fraction_theta_max 0.9751
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.082
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            66952
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_exptl_absorpt_coefficient_mu    1.039
_exptl_absorpt_correction_T_max  0.732
_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2736.00
_exptl_crystal_size_max          1.20
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.89
_refine_diff_density_min         -1.42
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  0 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.200(13)
_refine_ls_extinction_coef       240.3(16)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     839
_refine_ls_number_reflns         12797
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.4350\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0540
_reflns_number_gt                8114
_reflns_number_total             12824
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol0523291si20050926_023051.cif
_cod_data_source_block           '__2004-10-30'
_cod_original_cell_volume        5818.1(36)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C34 H40 Fe2 N2 O4 '
_cod_database_code               1506766