Formal [4 + 1]- and [5 + 1]-Annulation by an SN2–Conjugate Addition Sequence: Stereoselective Synthesis of Highly Substituted Carbocyles
Tong, Benny Meng Kiat; Chen, Hui; Chong, Sin Yee; Heng, Yi Li; Chiba, Shunsuke; Organic Letters 15 (2013) 6111–; doi:10.1021/ol4032842

data_1513162
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_section_title
;
 Formal [4 + 1]- and [5 + 1]-Annulation by an SN2--Conjugate Addition
 Sequence: Stereoselective Synthesis of Highly Substituted Carbocyles
;
_journal_issue                   23
_journal_name_full               'Organic Letters'
_journal_page_first              6111
_journal_paper_doi               10.1021/ol4032842
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C9 H18 O2'
_chemical_formula_weight         158.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   15.3408(8)
_cell_length_b                   44.262(2)
_cell_length_c                   5.1770(3)
_cell_measurement_reflns_used    5387
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      30.8346
_cell_measurement_theta_min      2.8105
_cell_volume                     3515.3(3)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       61
_diffrn_reflns_limit_k_min       -64
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15920
_diffrn_reflns_theta_full        31.06
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0508P)^2^+1.5499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                2676
_reflns_number_total             2820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol4032842_si_002.cif
_cod_data_source_block           I
_cod_database_code               1513162
_shelx_res_checksum              49773