Rhodium-catalyzed asymmetric tandem cyclization for efficient and rapid access to underexplored heterocyclic tertiary allylic alcohols containing a tetrasubstituted olefin.
Li, Yi; Xu, Ming-Hua; Organic letters 16 (2014) 2712–2715; doi:10.1021/ol500993h

data_1515758
_publ_section_title
;
 Rhodium-catalyzed asymmetric tandem cyclization for efficient and rapid
 access to underexplored heterocyclic tertiary allylic alcohols containing
 a tetrasubstituted olefin.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2712
_journal_page_last               2715
_journal_paper_doi               10.1021/ol500993h
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration S
_chemical_formula_sum            'C18 H16 Cl F O2'
_chemical_formula_weight         318.76
_space_group_IT_number           20
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.8770(11)
_cell_length_b                   12.0636(14)
_cell_length_c                   27.244(3)
_cell_measurement_temperature    296(2)
_cell_volume                     3246.2(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10662
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.249
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.270
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.270
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                3231
_reflns_number_total             3664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500993h_si_002.cif
_cod_data_source_block           2013366_0m
_cod_depositor_comments
'Adding full bibliography for 1515757--1515758.cif.'
_cod_original_cell_volume        3246.1(6)
_cod_original_sg_symbol_H-M      C2221
_cod_database_code               1515758