Diastereoselective, vinylogous mukaiyama aldol additions of silyloxy furans to cyclic ketones: annulation of butenolides and gamma-lactones.
Kong, Ke; Romo, Daniel; Organic letters 8 (2006) 2909–2912; doi:10.1021/ol060534q

data_1505960
_publ_section_title
;
 Diastereoselective, vinylogous mukaiyama aldol additions of silyloxy
 furans to cyclic ketones: annulation of butenolides and gamma-lactones.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2909
_journal_page_last               2912
_journal_paper_doi               10.1021/ol060534q
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26
_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                 94.519(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4828(14)
_cell_length_b                   8.2179(16)
_cell_length_c                   20.787(5)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      61.20
_cell_measurement_theta_min      4.27
_cell_volume                     1104.0(4)
_computing_cell_refinement
;
CELL_NOW (Sheldrick, 2003); SAINT (Bruker-Nonius 2003)
;
_computing_data_collection       'FRAMBO (BRUKER-NONIUS 2003)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'BRUKER GADDS D8 DISCOVER'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8959
_diffrn_reflns_theta_full        61.01
_diffrn_reflns_theta_max         61.01
_diffrn_reflns_theta_min         5.79
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  0.9180
_exptl_absorpt_correction_T_min  0.8394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2004)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0165(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0747P)^2^+0.1048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                1394
_reflns_number_total             1633
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060534qsi20060306_041924.cif
_cod_data_source_block           try2
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1505960