Pd-catalyzed enantioselective hydroalkoxylation of alkoxyallenes with phenol for construction of acyclic o,o-acetals.
Jiang, Liyin; Jia, Tao; Wang, Min; Liao, Jian; Cao, Peng; Organic letters 17 (2015) 1070–1073; doi:10.1021/acs.orglett.5b00146

data_1518998
_publ_section_title
;
 Pd-catalyzed enantioselective hydroalkoxylation of alkoxyallenes with
 phenol for construction of acyclic o,o-acetals.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1070
_journal_page_last               1073
_journal_paper_doi               10.1021/acs.orglett.5b00146
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-10
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_length_b                   8.5847(5)
_cell_length_c                   17.5470(5)
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      68.4730
_cell_measurement_theta_min      5.0310
_cell_volume                     1276.94(10)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_diffrn_ambient_temperature      294.39(10)
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_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details
;
  1 omega   40.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 25

  2 omega   -4.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 38

  3 omega  -24.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   87.0000  163.0000 25

  4 omega   85.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000    0.0000 26

  5 omega   43.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 29

  6 omega   24.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000    0.0000 26

  7 omega  -11.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 82

  8 omega   32.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 91

  9 omega   91.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 28

 10 omega   59.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -30.0000 64

 11 omega   35.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 55

 12 omega   34.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 36

 13 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 25

 14 omega  104.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 59

 15 omega   89.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 85

 16 omega  139.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000   60.0000 38

 17 omega   36.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000   60.0000 42

 18 omega   87.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 65
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0754808000
_diffrn_orient_matrix_UB_12      -0.1578610000
_diffrn_orient_matrix_UB_13      0.0205326000
_diffrn_orient_matrix_UB_21      0.0586488000
_diffrn_orient_matrix_UB_22      -0.0685776000
_diffrn_orient_matrix_UB_23      -0.0760122000
_diffrn_orient_matrix_UB_31      0.1545845000
_diffrn_orient_matrix_UB_32      -0.0508288000
_diffrn_orient_matrix_UB_33      0.0388148000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4326
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        65.815
_diffrn_reflns_theta_max         65.815
_diffrn_reflns_theta_min         5.041
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 598 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         1910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.1878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1086
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_reflns_Friedel_fraction_full    0.785
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_reflns_number_gt                1769
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00146_si_002.cif
_cod_data_source_block           0926
_cod_original_cell_volume        1276.95(10)
_cod_database_code               1518998
_reflns_odcompleteness_completeness 91.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C6(H6), C15(H15), C12(H12), C3(H3), C16(H16), C14(H14),
 C4(H4)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'