Diastereoselective construction of 7-methylenebicyclo[3.2.1]oct-3-en-2-one derivatives by palladium-catalyzed cyclization of propargylic acetates with 2-oxocyclohex-3-enecarboxylates.
Yoshida, Masahiro; Sugimura, Chiyuki; Shishido, Kozo; Organic letters 13 (2011) 3482–3485; doi:10.1021/ol201243u

data_1502271
_publ_section_title
;
 Diastereoselective construction of
 7-methylenebicyclo[3.2.1]oct-3-en-2-one derivatives by
 palladium-catalyzed cyclization of propargylic acetates with
 2-oxocyclohex-3-enecarboxylates.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3482
_journal_page_last               3485
_journal_paper_doi               10.1021/ol201243u
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C20 H22 O4 '
_chemical_formula_sum            'C20 H22 O4'
_chemical_formula_weight         326.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 91.738(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5532(7)
_cell_length_b                   12.7460(8)
_cell_length_c                   11.7436(7)
_cell_measurement_reflns_used    12508
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     1728.53(18)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16734
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696.00
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3926
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0020Fo^2^ + 1.0000\s(Fo^2^)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                2556
_reflns_number_total             3935
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol201243u_si_002.cif
_cod_data_source_block           '_CSA-1'
_cod_original_cell_volume        1728.5(2)
_cod_original_formula_sum        'C20 H22 O4 '
_cod_database_code               1502271