l-Proline-catalyzed direct intermolecular asymmetric aldol reactions of 1-phenylthiocycloalkyl carboxaldehydes with ketones. Easy access to spiro- and fused-cyclobutyl tetrahydrofurans and cyclopentanones.
Bernard, Angela M.; Frongia, Angelo; Guillot, Regis; Piras, Pier P.; Secci, Francesco; Spiga, Marco; Organic letters 9 (2007) 541–544; doi:10.1021/ol063084a

data_1505312
_publ_section_title
;
 l-Proline-catalyzed direct intermolecular asymmetric aldol reactions of
 1-phenylthiocycloalkyl carboxaldehydes with ketones. Easy access to
 spiro- and fused-cyclobutyl tetrahydrofurans and cyclopentanones.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              541
_journal_page_last               544
_journal_paper_doi               10.1021/ol063084a
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H18 O2 S'
_chemical_formula_sum            'C14 H18 O2 S'
_chemical_formula_weight         250.35
_chemical_name_systematic
4-hydroxy-4-[(1-phenylthio)cyclobutyl]-2-butanone
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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            4
_cell_length_a                   6.5872(2)
_cell_length_b                   9.5697(2)
_cell_length_c                   20.8343(5)
_cell_measurement_reflns_used    8453
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      41.18
_cell_measurement_theta_min      2.34
_cell_volume                     1313.34(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            30767
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         41.31
_diffrn_reflns_theta_min         1.95
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         8030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.0906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                7378
_reflns_number_total             8030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol063084asi20061218_031044.cif
_cod_data_source_block           503GuillotICMMO
_cod_database_code               1505312