A Catalytic Enantioselective Tandem Allylation Strategy for Rapid Terpene Construction: Application to the Synthesis of Pumilaside Aglycon
Grace E. Ferris; Kai Hong; Ian A. Roundtree; James P. Morken; Journal of the American Chemical Society 135 (2013) 2501–2504; doi:10.1021/ja400506j

data_4119383
_publ_section_title
;
 A Catalytic Enantioselective Tandem Allylation Strategy for Rapid Terpene
 Construction: Application to the Synthesis of Pumilaside Aglycon
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2501
_journal_page_last               2504
_journal_paper_doi               10.1021/ja400506j
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H26 O2'
_chemical_formula_sum            'C19 H26 O2'
_chemical_formula_weight         286.40
_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                 91.863(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5973(10)
_cell_length_b                   7.2630(10)
_cell_length_c                   13.3032(16)
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.16
_cell_measurement_theta_min      6.95
_cell_volume                     830.24(18)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9045
_diffrn_reflns_theta_full        65.43
_diffrn_reflns_theta_max         65.43
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0102(17)
_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   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0465P)^2^+0.2406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                2372
_reflns_number_total             2711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja400506j_si_004.cif
_cod_data_source_block           C19H26O2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4119383