Diastereoselective, Three-Component Cascade Synthesis of Tetrahydrofurans and Tetrahydropyrans Employing the Tandem Mukaiyama Aldol–Lactonization Process
T. Andrew Mitchell; Cunxiang Zhao; Daniel Romo; Journal of Organic Chemistry 73 (2008) 9544–9551; doi:10.1021/jo801604k

data_4023927
_publ_section_title
;
 Diastereoselective, Three-Component Cascade Synthesis of
 Tetrahydrofurans and Tetrahydropyrans Employing the Tandem
 Mukaiyama Aldol--Lactonization Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9544
_journal_page_last               9551
_journal_paper_doi               10.1021/jo801604k
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H25 Br O4'
_chemical_formula_weight         433.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 115.272(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.996(16)
_cell_length_b                   5.709(5)
_cell_length_c                   20.557(17)
_cell_measurement_reflns_used    5789
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.19
_cell_volume                     2016(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0709
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20029
_diffrn_reflns_theta_full        27.64
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    2.063
_exptl_absorpt_correction_T_max  0.8203
_exptl_absorpt_correction_T_min  0.4252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0414P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                3050
_reflns_number_total             4500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801604k_si_002.cif
_cod_data_source_block           drb1127b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023927