Asymmetric cinnamylation of N-tert-butanesulfinyl imines with cinnamyl acetates: total syntheses of (+)-lycoricidine and (+)-7-deoxypancratistatin.
Cai, Sen-Lin; Yuan, Bin-Hua; Jiang, Yi-Xiang; Lin, Guo-Qiang; Sun, Xing-Wen; Chemical communications (Cambridge, England) 53 (2017) 3520–3523; doi:10.1039/c7cc00108h

data_7119687
_publ_section_title
;
 Asymmetric cinnamylation of N-tert-butanesulfinyl imines with cinnamyl
 acetates: total syntheses of (+)-lycoricidine and
 (+)-7-deoxypancratistatin.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3520
_journal_page_last               3523
_journal_paper_doi               10.1039/c7cc00108h
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C17 H19 N O7'
_chemical_formula_weight         349.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-23 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5766(15)
_cell_length_b                   8.3899(7)
_cell_length_c                   9.3442(7)
_cell_measurement_reflns_used    3959
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.00
_cell_measurement_theta_min      4.52
_cell_volume                     1534.7(2)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.955
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7562
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.995
_diffrn_reflns_theta_min         4.517
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 943 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2648
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.0682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                2522
_reflns_number_total             2648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc00108h2.cif
_cod_data_source_block           cu_60530ba
_cod_depositor_comments
'Adding full bibliography for 7119686--7119687.cif.'
_cod_database_code               7119687
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.753
_shelx_estimated_absorpt_t_max   0.825
_shelx_res_checksum              91057