DAST-mediated cyclization of α,α-disubstituted-α-acylaminoketones: efficient and divergent synthesis of unprecedented heterocycles.
Bigot, Aurélien; Blythe, Judith; Pandya, Chirag; Wagner, Trixie; Loiseleur, Olivier; Organic letters 13 (2011) 192–195; doi:10.1021/ol102454e

data_1501854
_publ_section_title
;
 DAST-mediated cyclization of \a,\a-disubstituted-\a-acylaminoketones:
 efficient and divergent synthesis of unprecedented heterocycles.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              192
_journal_page_last               195
_journal_paper_doi               10.1021/ol102454e
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C17 H17 N3'
_chemical_formula_weight         263.34
_chemical_name_common            ABIV-284
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 116.024(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.632(3)
_cell_length_b                   9.666(2)
_cell_length_c                   12.804(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1404.9(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27775
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.7867
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4855
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.1911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0642
_reflns_number_gt                4803
_reflns_number_total             4855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102454e_si_005.cif
_cod_data_source_block           OLO26a
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1501854
_chemical_source_common          ACT