Enantioselective Synthesis of α-Allyl-α-aryldihydrocoumarins and 3-Isochromanones via Pd-Catalyzed Decarboxylative Asymmetric Allylic Alkylation.
Akula, Ramulu; Guiry, Patrick J.; Organic letters 18 (2016) 5472–5475; doi:10.1021/acs.orglett.6b02584

data_1555821
_publ_section_title
;
 Enantioselective Synthesis of \a-Allyl-\a-aryldihydrocoumarins and
 3-Isochromanones via Pd-Catalyzed Decarboxylative Asymmetric Allylic
 Alkylation.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5472
_journal_page_last               5475
_journal_paper_doi               10.1021/acs.orglett.6b02584
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H22 O5'
_chemical_formula_sum            'C21 H22 O5'
_chemical_formula_weight         354.39
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 101.606(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4714(1)
_cell_length_b                   6.24720(6)
_cell_length_c                   17.1326(3)
_cell_measurement_reflns_used    9540
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4590
_cell_measurement_theta_min      5.3310
_cell_volume                     888.16(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18266
_diffrn_reflns_theta_full        76.61
_diffrn_reflns_theta_max         76.61
_diffrn_reflns_theta_min         5.27
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3700
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0426P)^2^+0.1316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0723
_reflns_number_gt                3572
_reflns_number_total             3700
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol6b02584_si_001.cif
_cod_data_source_block           gui132
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555821