Asymmetric [3+2] annulation of allenes with maleimides catalyzed by dipeptide-derived phosphines: facile creation of functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers
Qianyi Zhao; Xiaoyu Han; Yin Wei; Min Shi; Yixin Lu; Chem.Commun. 48 (2012) 970–; doi:10.1039/c2cc16904e

data_7107210
_publ_section_title
;
 Asymmetric [3+2] annulation of allenes with maleimides catalyzed by
 dipeptide-derived phosphines: facile creation of functionalized bicyclic
 cyclopentenes containing two tertiary stereogenic centers
;
_journal_name_full               Chem.Commun.
_journal_page_first              970
_journal_paper_doi               10.1039/c2cc16904e
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H18 Br F2 N O2'
_chemical_formula_weight         422.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 104.482(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2224(14)
_cell_length_b                   10.4748(16)
_cell_length_c                   10.2384(16)
_cell_measurement_reflns_used    1431
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.950
_cell_measurement_theta_min      4.562
_cell_volume                     957.6(3)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0855
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5612
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    2.178
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.1181
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.451
_exptl_crystal_size_min          0.397
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.233
_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   0.079(10)
_refine_ls_extinction_coef       0.0185(19)
_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   0.887
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3850
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0402
_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
[0.00000+1.00000exp(2.00(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0463P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.1005
_reflns_number_gt                1787
_reflns_number_total             3850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc16904e.txt
_cod_data_source_block           cd201373
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7107210