A Dual Lewis Base Activation Strategy for Enantioselective Carbene-Catalyzed Annulations
Javier Izquierdo; Ane Orue; Karl A. Scheidt; Journal of the American Chemical Society 135 (2013) 10634–10637; doi:10.1021/ja405833m

data_4120166
_publ_section_title
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 A Dual Lewis Base Activation Strategy for Enantioselective
 Carbene-Catalyzed Annulations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10634
_journal_page_last               10637
_journal_paper_doi               10.1021/ja405833m
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'B F4, C22 H24 N3 O'
_chemical_formula_sum            'C22 H24 B F4 N3 O'
_chemical_formula_weight         433.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9050(3)
_cell_length_b                   11.2173(3)
_cell_length_c                   18.9185(6)
_cell_measurement_reflns_used    6228
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.838
_cell_measurement_theta_min      4.582
_cell_volume                     2101.98(11)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7869
_diffrn_reflns_theta_full        64.94
_diffrn_reflns_theta_max         64.94
_diffrn_reflns_theta_min         4.58
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0731 before and 0.0362 after correction.
The Ratio of minimum to maximum transmission is 0.9035.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       rod
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0287P)^2^+0.4038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0624
_reflns_number_gt                3142
_reflns_number_total             3277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja405833m_si_001.cif
_cod_data_source_block           cu_jizquierdo06_11_0m
_cod_database_code               4120166
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. others
 Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(H21A)=Sof(H21B)=Sof(C22A)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C19(H19A,H19B), C21(H21C,H21D), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22A(H22A,H22B,H22C), C22B(H22D,H22E,H22F)
;