Gold-catalyzed intramolecular hydroamination of o-alkynylbenzyl carbamates: a route to chiral fluorinated isoindoline and isoquinoline derivatives.
Fustero, Santos; Ibáñez, Ignacio; Barrio, Pablo; Maestro, Miguel A.; Catalán, Silvia; Organic letters 15 (2013) 832–835; doi:10.1021/ol3035142

data_1556144
_publ_section_title
;
 Gold-catalyzed intramolecular hydroamination of o-alkynylbenzyl
 carbamates: a route to chiral fluorinated isoindoline and isoquinoline
 derivatives.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              832
_journal_page_last               835
_journal_paper_doi               10.1021/ol3035142
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 F5 N O2'
_chemical_formula_sum            'C21 H20 F5 N O2'
_chemical_formula_weight         413.38
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5446(2)
_cell_length_b                   14.1930(4)
_cell_length_c                   17.9736(6)
_cell_measurement_temperature    100(2)
_cell_volume                     1924.62(10)
_computing_cell_refinement       'SAINT V7.12A (Bruker 2004)'
_computing_data_collection       'Apex2 V.1.0-27(Bruker 2005)'
_computing_data_reduction        'SAINT and XPREP Version 6.14, 2003'
_computing_molecular_graphics    'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_publication_material  'Bruker SHELXTL suite ver. 6.12, 2001'
_computing_structure_refinement  'SHELXL-97 in SHELXTL  ver. 6.12, 2001'
_computing_structure_solution    'SHELXS-97 in SHELXTL ver. 6.12, 2001'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            45330
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS program multi-scan
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.5104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                3098
_reflns_number_total             3402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3035142_si_001.cif
_cod_data_source_block           anc1
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1556144