Mild and Selective Hydrozirconation of Amides to Aldehydes Using Cp2Zr(H)Cl: Scope and Mechanistic Insight
Jared T. Spletstoser; Jonathan M. White; Ashok Rao Tunoori; Gunda I. Georg; Journal of the American Chemical Society 129 (2007) 3408–3419; doi:10.1021/ja066362+

data_4111325
_publ_contact_author
; 
   Prof. Gunda I. Georg 
   Department of Medicinal Chemistry -- University of Kansas 
   Malott Hall 
   1251 Wescoe Hall Dr, Rm 4070 
   Lawrence, KS  66045-7582  USA 
;
_publ_contact_author_email       georg@ku.edu
_publ_contact_author_fax         1(785)8645326
_publ_contact_author_phone       1(785)8644498
_publ_section_title
;
 Mild and Selective Hydrozirconation of Amides to Aldehydes Using
 Cp2Zr(H)Cl: Scope and Mechanistic Insight
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3408
_journal_page_last               3419
_journal_paper_doi               10.1021/ja066362+
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C20 H20 Cl2 O Zr2'
_chemical_formula_sum            'C20 H20 Cl2 O Zr2'
_chemical_formula_weight         529.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   7.8384(4)
_cell_length_b                   7.8384(4)
_cell_length_c                   27.668(3)
_cell_measurement_reflns_used    4547
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.00
_cell_volume                     1472.19(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       '\w 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  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1939
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_T_max  0.9240
_exptl_absorpt_correction_T_min  0.7056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sheldrick, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             786
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.090
_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   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.0600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0709
_reflns_number_gt                1905
_reflns_number_total             1939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja066362si20060901_070946.cif
_cod_data_source_block           04001
_cod_original_cell_volume        1472.19(18)
_cod_database_code               4111325