Allylsamarium Bromide-Mediated Cascade Cyclization of Homoallylic Esters. Synthesis of 2-(2-Hydroxyalkyl)cyclopropanols and 2-(2-Hydroxyethyl)bicyclo[2.1.1]hexan-1-ols.
Shen, Mengmeng; Tu, Yawei; Xie, Guanqun; Niu, Qingsheng; Mao, Hui; Xie, Tingting; Flowers, 2nd, Robert A; Lv, Xin; Wang, Xiaoxia; The Journal of organic chemistry 80 (2014) 52–; doi:10.1021/jo501797w

data_4030372
_publ_section_title
;
 Allylsamarium Bromide-Mediated Cascade Cyclization of Homoallylic Esters.
 Synthesis of 2-(2-Hydroxyalkyl)cyclopropanols and
 2-(2-Hydroxyethyl)bicyclo[2.1.1]hexan-1-ols.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              52
_journal_paper_doi               10.1021/jo501797w
_journal_volume                  80
_journal_year                    2014
_chemical_formula_sum            'C14 H18 N0 O2'
_chemical_formula_weight         218.28
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
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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            8
_cell_length_a                   8.4068(5)
_cell_length_b                   11.7148(6)
_cell_length_c                   24.5654(14)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.66
_cell_volume                     2419.3(2)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w 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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10862
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  .0000
_exptl_absorpt_correction_T_min  .0000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             944
_exptl_crystal_size_max          .351
_exptl_crystal_size_mid          .257
_exptl_crystal_size_min          .159
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.815
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1106P)^2^+0.6311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                1885
_reflns_number_total             2738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501797w_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030372.cif.
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4030372
_refine_ls_r_factor_ref          0.0688