Regio- and Diastereoselective Synthesis of Dihydropyrans and Pyranopyrans via Oxonium-Ene Reaction of β-Allenols and Aldehydes.
Devi, Ngangbam Renubala; Sultana, Sabera; Borah, Madhurjya; Saikia, Anil K.; The Journal of organic chemistry 83 (2018) 14987–14998; doi:10.1021/acs.joc.8b02244

data_4034730
_publ_section_title
;
 Regio- and Diastereoselective Synthesis of Dihydropyrans and Pyranopyrans
 via Oxonium-Ene Reaction of \b-Allenols and Aldehydes.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14987
_journal_page_last               14998
_journal_paper_doi               10.1021/acs.joc.8b02244
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.160(12)
_cell_angle_beta                 90.233(11)
_cell_angle_gamma                90.152(12)
_cell_formula_units_Z            4
_cell_length_a                   7.3532(13)
_cell_length_b                   12.219(2)
_cell_length_c                   15.266(3)
_cell_measurement_reflns_used    3573
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.9250
_cell_measurement_theta_min      3.7090
_cell_volume                     1360.9(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13594
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0520
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1732
_reflns_number_gt                2529
_reflns_number_total             4676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02244_si_004.cif
_cod_data_source_block           rb-cy5no2-f
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4034730