Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from allenoates and aldehydes: an observation of phosphine-induced chemoselectivity.
Xu, Silong; Zou, Wen; Wu, Guiping; Song, Haibin; He, Zhengjie; Organic letters 12 (2010) 3556–3559; doi:10.1021/ol101429z

data_1503119
_publ_section_title
;
 Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from
 allenoates and aldehydes: an observation of phosphine-induced
 chemoselectivity.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3556
_journal_page_last               3559
_journal_paper_doi               10.1021/ol101429z
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C18 H22 O4'
_chemical_formula_sum            'C18 H22 O4'
_chemical_formula_weight         302.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.888(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.985(3)
_cell_length_b                   7.5030(14)
_cell_length_c                   15.386(3)
_cell_measurement_reflns_used    2084
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      72.6
_cell_measurement_theta_min      27.6
_cell_volume                     1636.7(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 11.11
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16873
_diffrn_reflns_theta_full        67.75
_diffrn_reflns_theta_max         72.64
_diffrn_reflns_theta_min         3.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  0.8397
_exptl_absorpt_correction_T_min  0.7877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       0.034(2)
_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   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0935P)^2^+0.3008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                2890
_reflns_number_total             3188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101429z_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               1503119