Carbene catalyzed umpolung of α,β-enals: a reactivity study of diamino dienols vs. azolium enolates, and the characterization of advanced reaction intermediates
Yatham, Veera Reddy; Neudörfl, Jörg-M.; Schlörer, Nils E.; Berkessel, Albrecht; Chem. Sci. 6 (2015) 3706–; doi:10.1039/C5SC01027F

data_1519389
_publ_section_title
;
 Carbene catalyzed umpolung of \a,\b-enals: a reactivity study of diamino
 dienols vs. azolium enolates, and the characterization of advanced
 reaction intermediates
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              3706
_journal_paper_doi               10.1039/C5SC01027F
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C48 H58 N2 O4, 2(C6 H6)'
_chemical_formula_sum            'C60 H70 N2 O4'
_chemical_formula_weight         883.18
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-07-22 deposited with the CCDC.
2015-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                75.286(7)
_cell_angle_beta                 86.422(6)
_cell_angle_gamma                86.274(8)
_cell_formula_units_Z            2
_cell_length_a                   10.8676(15)
_cell_length_b                   12.3446(16)
_cell_length_c                   19.476(3)
_cell_measurement_reflns_used    9490
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.08
_cell_volume                     2518.9(6)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.1412
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9490
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.08
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .04
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         8128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1456
_reflns_number_gt                3947
_reflns_number_total             8128
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc01027f2.cif
_cod_data_source_block           z3
_cod_depositor_comments
'Adding full bibliography for 1519389--1519390.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519389