A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs
Guobi Chai; Shangze Wu; Chunling Fu; Shengming Ma; Journal of the American Chemical Society 133 (2011) 3740–3743; doi:10.1021/ja1108694

data_4105775
_publ_section_title
;
 A Straightforward Synthesis of Cyclobutenones via a Tandem Michael
 Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3740
_journal_page_last               3743
_journal_paper_doi               10.1021/ja1108694
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C17 H24 O'
_chemical_formula_sum            'C17 H24 O'
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_atom_sites_solution_primary     direct
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_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.767(5)
_cell_angle_beta                 71.089(5)
_cell_angle_gamma                70.386(6)
_cell_formula_units_Z            8
_cell_length_a                   12.2850(8)
_cell_length_b                   16.5578(10)
_cell_length_c                   16.7837(8)
_cell_measurement_reflns_used    5782
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8490
_cell_measurement_theta_min      2.8232
_cell_volume                     2996.6(3)
_computing_cell_refinement
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
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_computing_molecular_graphics
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 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23881
_diffrn_reflns_theta_full        66.96
_diffrn_reflns_theta_max         66.96
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
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;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET)
(compiled Nov 17 2009,16:58:22)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    ref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         10528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0717
_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 w=1/[\s^2^(Fo^2^)+(0.1343P)^2^+0.2512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2317
_reflns_number_gt                6270
_reflns_number_total             10528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1108694_si_001.cif
_cod_data_source_block           100522_fucl
_cod_database_code               4105775