AgOTf-catalyzed cascade annulation of 5-hexyn-1-ols and aldehydes: enabling the diastereoselective synthesis of [6,6,6]-trioxa-fused ketals and hexahydro-2<i>H</i>-chromenes.
Vinodkumar, Ramavath; Nakate, Ashwini K.; Krishna, Gamidi Rama; Kontham, Ravindar; Chemical communications (Cambridge, England) 61 (2025) 973–976; doi:10.1039/d4cc05546b

data_7134046
_publ_section_title
;
 AgOTf-catalyzed cascade annulation of 5-hexyn-1-ols and aldehydes:
 enabling the diastereoselective synthesis of [6,6,6]-trioxa-fused ketals
 and hexahydro-2<i>H</i>-chromenes.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              973
_journal_page_last               976
_journal_paper_doi               10.1039/d4cc05546b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C19 H26 O3'
_chemical_formula_weight         302.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-02-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7312(11)
_cell_length_b                   16.422(2)
_cell_length_c                   11.2564(15)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.19
_cell_volume                     1614.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            65854
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.991
_diffrn_reflns_theta_min         2.642
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       Plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.6901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3313
_reflns_number_total             3515
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {56b90ed7-7997-4b82-80de-6359957c7730}
_cod_data_source_file            d4cc05546b2.cif
_cod_data_source_block           5aa
_cod_depositor_comments
'Adding full bibliography for 7134046--7134049.cif.'
_cod_database_code               7134046
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              5113
_shelx_hkl_checksum              25870
_publcif_funding_html
;
;