Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of β'-Acetoxy Allenoate: Highly Stereoselective Access to 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine.
Gu, Yiting; Hu, Pengfei; Ni, Chunjie; Tong, Xiaofeng; Journal of the American Chemical Society 137 (2015) 6400–6406; doi:10.1021/jacs.5b03273

data_4123689
_publ_section_title
;
 Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of
 \b'-Acetoxy Allenoate: Highly Stereoselective Access to
 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6400
_journal_page_last               6406
_journal_paper_doi               10.1021/jacs.5b03273
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C29 H21 Br2 N O3'
_chemical_formula_weight         591.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.331(4)
_cell_angle_beta                 107.656(3)
_cell_angle_gamma                91.586(4)
_cell_formula_units_Z            4
_cell_length_a                   10.4205(15)
_cell_length_b                   15.529(2)
_cell_length_c                   16.859(2)
_cell_measurement_reflns_used    1211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.299
_cell_measurement_theta_min      4.831
_cell_volume                     2547.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0523
_diffrn_reflns_av_sigmaI/netI    0.1388
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14912
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    3.213
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         9444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.1718
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc 
 [0.00000+1.00000exp(2.00(sin\q/\l)^2^)]/ 
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0523P)^2^+0.0000sin\q/\l] 
 where P = 0.33333Fo^2^ + 0.66667Fc^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                3947
_reflns_number_total             9444
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b03273_si_002.cif
_cod_data_source_block           cd214248
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4123688--4123689.cif.
;
_cod_original_cell_volume        2547.5(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4123689