Enantioselective synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by nickel-catalyzed denitrogenative annulation of 1,2,3-benzotriazin-4(3H)-ones with allenes.
Yamauchi, Motoshi; Morimoto, Masao; Miura, Tomoya; Murakami, Masahiro; Journal of the American Chemical Society 132 (2010) 54–55; doi:10.1021/ja909603j

data_4101646
_publ_contact_author_address
;
Department of Synthetic Chemistry and Biological Chemistry,
Graduate School of Engineering, Kyoto University,
;
_publ_contact_author_email       ' murakami_at_sbchem.kyoto-u.ac.jp '
_publ_contact_author_fax         ' +81-75-383-2747 '
_publ_contact_author_name        ' Masahiro Murakami '
_publ_contact_author_phone       ' +81-75-383-2748 '
_publ_section_title
;
 Enantioselective synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by
 nickel-catalyzed denitrogenative annulation of
 1,2,3-benzotriazin-4(3H)-ones with allenes.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              54
_journal_page_last               55
_journal_paper_doi               10.1021/ja909603j
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C44 H35 N Ni O P2'
_chemical_formula_weight         714.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.9745(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3776(3)
_cell_length_b                   14.4722(4)
_cell_length_c                   19.9190(6)
_cell_measurement_temperature    296(2)
_cell_volume                     3563.31(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            52234
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.6162
_exptl_absorpt_correction_T_min  0.6162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         8134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0402P)^2^+1.1180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                7144
_reflns_number_total             8134
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja909603j_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        3563.30(17)
_cod_original_sg_symbol_Hall     -p_2yn
_cod_original_sg_symbol_H-M      p_21/n
_cod_database_code               4101646