Organometallic Enantiomeric Scaffolding. Sequential Semipinacol/1,5-"Michael-like" Reactions as a Strategic Approach to Bridgehead-Quaternary Center Aza[3.3.1]Bicyclics: Application to the Total Synthesis of (-)-Adaline
Thomas C. Coombs; Yongqiang Zhang; Ethel C. Garnier-Amblard; Lanny S. Liebeskind; Journal of the American Chemical Society 131 (2009) 876–877; doi:10.1021/ja808533z

data_4103821
_publ_section_title
;
 Organometallic Enantiomeric Scaffolding. Sequential
 Semipinacol/1,5-"Michael-like" Reactions as a Strategic Approach to
 Bridgehead-Quaternary Center Aza[3.3.1]Bicyclics: Application to the
 Total Synthesis of (-)-Adaline
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              876
_journal_page_last               877
_journal_paper_doi               10.1021/ja808533z
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C29 H29 B Mo N7 O6'
_chemical_formula_weight         678.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           82
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.1763(14)
_cell_length_b                   21.1763(14)
_cell_length_c                   12.8350(10)
_cell_measurement_reflns_used    5664
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.16
_cell_measurement_theta_min      2.67
_cell_volume                     5755.7(7)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.863
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0861
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29240
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.828000
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irreg
_exptl_crystal_F_000             2776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0190P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                5215
_reflns_number_total             6173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808533z_si_003.cif
_cod_data_source_block           zyq594si
_cod_database_code               4103821