Asymmetric Construction of 2,3-Dihydroisoxazoles via an Organocatalytic Formal [3 + 2] Cycloaddition of Enynes with N-Hydroxylamines.
Li, Wenbo; Yu, Xiuzhao; Yue, Zhenting; Zhang, Junliang; Organic letters 18 (2016) 3972–3975; doi:10.1021/acs.orglett.6b01737

data_1555645
_publ_section_title
;
 Asymmetric Construction of 2,3-Dihydroisoxazoles via an Organocatalytic
 Formal [3 + 2] Cycloaddition of Enynes with N-Hydroxylamines.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3972
_journal_page_last               3975
_journal_paper_doi               10.1021/acs.orglett.6b01737
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H29 N O2'
_chemical_formula_weight         411.52
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.09750(10)
_cell_length_b                   10.80700(10)
_cell_length_c                   40.2707(4)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      138.401
_cell_measurement_theta_min      6.585
_cell_volume                     2218.46(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            13899
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.487
_diffrn_reflns_theta_min         2.194
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 1506 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.4512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                3773
_reflns_number_total             3825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01737_si_002.cif
_cod_data_source_block           cu_dm16479_0m
_cod_database_code               1555645
_shelx_estimated_absorpt_t_min   0.890
_shelx_estimated_absorpt_t_max   0.937
_shelxl_version_number           2013-4
_shelx_res_checksum              24915
_shelx_hkl_checksum              44976