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_1506768
_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_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C30 H40 Fe2 N2 O2 '
_chemical_formula_sum            'C30 H40 Fe2 N2 O2'
_chemical_formula_weight         572.35
_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            4
_cell_length_a                   11.484(5)
_cell_length_b                   12.169(6)
_cell_length_c                   18.868(9)
_cell_measurement_reflns_used    7075
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     2637(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SHELXS97
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9968
_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  0.098
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19904
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.52
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     362
_refine_ls_number_reflns         1690
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0006Fo^2^ + 2.0500\s(Fo^2^)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0620
_reflns_number_gt                1690
_reflns_number_total             3390
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol0523291si20050926_024019.cif
_cod_data_source_block           '__20050118'
_cod_original_cell_volume        2636.7(22)
_cod_original_formula_sum        'C30 H40 Fe2 N2 O2 '
_cod_database_code               1506768