Copper(II)-Catalyzed Asymmetric Henry Reaction of o-Alkynylbenzaldehydes Followed by Gold(I)-Mediated Cycloisomerization: An Enantioselective Route to Chiral 1H-Isochromenes and 1,3-Dihydroisobenzofurans
Dengfu Lu; Yirong Zhou; Yajun Li; Shaobai Yan; Yuefa Gong; Journal of Organic Chemistry 76 (2011) 8869–8878; doi:10.1021/jo201596p

data_4026701
_publ_section_title
;
 Copper(II)-Catalyzed Asymmetric Henry Reaction of o-Alkynylbenzaldehydes
 Followed by Gold(I)-Mediated Cycloisomerization: An Enantioselective
 Route to Chiral 1H-Isochromenes and 1,3-Dihydroisobenzofurans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8869
_journal_page_last               8878
_journal_paper_doi               10.1021/jo201596p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27
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_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5668(8)
_cell_length_b                   8.5894(13)
_cell_length_c                   27.730(4)
_cell_measurement_reflns_used    680
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      17.64
_cell_measurement_theta_min      2.48
_cell_volume                     1325.9(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
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_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9852
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0683
_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^)+(0.0269P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                1626
_reflns_number_total             2620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201596p_si_004.cif
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