Phosphine-catalyzed cascade [3 + 2] cyclization-allylic alkylation, [2 + 2 + 1] annulation, and [3 + 2] cyclization reactions between allylic carbonates and enones.
Zhou, Rong; Wang, Jianfang; Song, Haibin; He, Zhengjie; Organic letters 13 (2011) 580–583; doi:10.1021/ol102738b

data_1501895
_publ_section_title
;
 Phosphine-catalyzed cascade [3 + 2] cyclization-allylic alkylation, [2 +
 2 + 1] annulation, and [3 + 2] cyclization reactions between allylic
 carbonates and enones.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              580
_journal_page_last               583
_journal_paper_doi               10.1021/ol102738b
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C31 H35 Cl O5'
_chemical_formula_sum            'C31 H35 Cl O5'
_chemical_formula_weight         523.04
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.267(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6970(14)
_cell_length_b                   14.3290(13)
_cell_length_c                   14.3030(13)
_cell_measurement_reflns_used    8813
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      1.50
_cell_volume                     2919.2(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27668
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         6908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0554
_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 w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                5318
_reflns_number_total             6908
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102738b_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               1501895