Diastereoselective synthesis of isochromans via the Cu(ii)-catalysed intramolecular Michael-type trapping of oxonium ylides.
Alavala, Gopi Krishna Reddy; Sajjad, Farrukh; Shi, Taoda; Kang, Zhenghui; Ma, Mingliang; Xing, Dong; Hu, Wenhao; Chemical communications (Cambridge, England) 54 (2018) 12650–12653; doi:10.1039/c8cc06390g

data_7122498
_publ_section_title
;
 Diastereoselective synthesis of isochromans via the Cu(ii)-catalysed
 intramolecular Michael-type trapping of oxonium ylides.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12650
_journal_page_last               12653
_journal_paper_doi               10.1039/c8cc06390g
_journal_volume                  54
_journal_year                    2018
_chemical_compound_source        'Synthesized compound'
_chemical_formula_moiety         'C25 H22 O4'
_chemical_formula_sum            'C25 H22 O4'
_chemical_formula_weight         386.42
_chemical_name_common
'methyl (3R,4S)-4-(2-oxo-2-phenylethyl)-3-phenylisochromane-3-carboxylate'
_chemical_name_systematic
'methyl (3R,4S)-4-(2-oxo-2-phenylethyl)-3-phenylisochromane-3-carboxylate'
_chemical_properties_physical    'The compound is stable at ambient conditions'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     dual
_audit_creation_date             2017-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-06-15 deposited with the CCDC.
2018-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.330(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6081(6)
_cell_length_b                   6.1955(2)
_cell_length_c                   21.7106(8)
_cell_measurement_reflns_used    4972
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8740
_cell_measurement_theta_min      4.1000
_cell_volume                     2004.11(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -25.00   2.00   1.00    3.00    --    0.00 -38.00-120.00   27
  2  \w     16.00  89.00   1.00    3.00    --    0.00  57.00   0.00   73
  3  \w    -85.00  19.00   1.00    3.00    --    0.00 -38.00 120.00  104
  4  \w    -87.00 -34.00   1.00    3.00    --    0.00 -82.00  90.00   53
  5  \w     30.00  66.00   1.00    3.00    --    0.00  19.00-120.00   36
  6  \w    -42.00  -9.00   1.00    3.00    --    0.00 -38.00-150.00   33
  7  \w     76.00 108.00   1.00   10.00    --   95.80 -82.00  60.00   32
  8  \w     16.00  72.00   1.00   10.00    --   95.80 -82.00  60.00   56
  9  \w     23.00 127.00   1.00   10.00    --   95.80 -82.00 150.00  104
 10  \w      6.00  31.00   1.00   10.00    --   95.80 -82.00 -90.00   25
 11  \w     57.00 128.00   1.00   10.00    --   95.80 -82.00 -90.00   71
 12  \w      7.00  97.00   1.00   10.00    --   95.80 -61.00  60.00   90
 13  \w      7.00 120.00   1.00   10.00    --   95.80 -61.00 150.00  113
 14  \w      6.00 114.00   1.00   10.00    --   95.80 -45.00 -90.00  108
 15  \w    115.00 164.00   1.00   10.00    --   95.80  30.00-120.00   49
 16  \w     66.00 113.00   1.00   10.00    --   95.80 -30.00 -90.00   47
 17  \w     60.00  96.00   1.00   10.00    --   95.80 -82.00   0.00   36
 18  \w     28.00  55.00   1.00   10.00    --   95.80 -30.00 -90.00   27
 19  \w     17.00  98.00   1.00   10.00    --   95.80 -30.00-180.00   81
 20  \w    113.00 178.00   1.00   10.00    --   95.80   0.00 -60.00   65
 21  \w      6.00  77.00   1.00   10.00    --   95.80   0.00 -60.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0872933000
_diffrn_orient_matrix_UB_12      0.0880871000
_diffrn_orient_matrix_UB_13      0.0472713000
_diffrn_orient_matrix_UB_21      -0.0429914000
_diffrn_orient_matrix_UB_22      -0.0110244000
_diffrn_orient_matrix_UB_23      0.0552572000
_diffrn_orient_matrix_UB_31      0.0351149000
_diffrn_orient_matrix_UB_32      -0.2321669000
_diffrn_orient_matrix_UB_33      0.0153879000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16400
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.022
_diffrn_reflns_theta_max         67.022
_diffrn_reflns_theta_min         4.138
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0630P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2431
_reflns_number_total             3564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06390g2.cif
_cod_data_source_block           exp_100
_cod_depositor_comments          'Adding full bibliography for 7122498.cif.'
_cod_database_code               7122498
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.885
_reflns_odcompleteness_completeness 99.92
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              39643
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.199
_oxdiff_exptl_absorpt_empirical_full_min 0.424