Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Oxiranes: A Diastereoselective Method for the Synthesis of 7-Hydroxy-2,3,5-trienoates.
Kuş, Melih; Artok, Levent; Aygün, Muhittin; The Journal of organic chemistry 80 (2015) 5494–5506; doi:10.1021/acs.joc.5b00382

data_4030998
_publ_section_title
;
 Palladium-Catalyzed Alkoxycarbonylation of Conjugated Enyne Oxiranes: A
 Diastereoselective Method for the Synthesis of
 7-Hydroxy-2,3,5-trienoates.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5494
_journal_page_last               5506
_journal_paper_doi               10.1021/acs.joc.5b00382
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H28 N O5'
_chemical_formula_sum            'C22 H29 N O5'
_chemical_formula_weight         387.46
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_angle_alpha                90.00
_cell_angle_beta                 92.857(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3053(13)
_cell_length_b                   23.4741(16)
_cell_length_c                   7.5861(9)
_cell_measurement_reflns_used    1580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3840
_cell_measurement_theta_min      3.5330
_cell_volume                     2188.6(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0038703000
_diffrn_orient_matrix_UB_12      0.0252684000
_diffrn_orient_matrix_UB_13      0.0511731000
_diffrn_orient_matrix_UB_21      0.0573384000
_diffrn_orient_matrix_UB_22      -0.0002160000
_diffrn_orient_matrix_UB_23      -0.0057734000
_diffrn_orient_matrix_UB_31      -0.0051385000
_diffrn_orient_matrix_UB_32      0.0165675000
_diffrn_orient_matrix_UB_33      -0.0782105000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11919
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.7483
_exptl_crystal_size_mid          0.1509
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.0676
_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^)+(0.0788P)^2^+0.1211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1984
_reflns_number_gt                2069
_reflns_number_total             4477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00382_si_002.cif
_cod_data_source_block           smart
_cod_depositor_comments          'Adding full bibliography for 4030998.cif.'
_cod_database_code               4030998
_chemical_oxdiff_formula         'C14 H22 O4'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C14(H14), C17(H17), C20(H20), C21(H21), C23(H23), C25(H25), C26(H26),
 C28(H28)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C24(H24A,H24B,H24C), C27(H27A,H27B,
 H27C)
;