Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes: Access to Defined Configured Stereotriads, Tetrads, and Stereopentads
Kerstin Rohr; Robert Herre; Rainer Mahrwald; Journal of Organic Chemistry 74 (2009) 3744–3749; doi:10.1021/jo9003635

data_4024540
_publ_section_title
;
Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes:
Access to Defined Configured Stereotriads, Tetrads, and Stereopentads
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3744
_journal_page_last               3749
_journal_paper_doi               10.1021/jo9003635
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H36 O5 Si'
_chemical_formula_sum            'C18 H36 O5 Si'
_chemical_formula_weight         360.56
_chemical_name_systematic
; 
  (4S,5S,6S)-6-(tert-butyldimethylsilyloxy)-6-((S)-2,2-
dimetyhl-1,3-dioxolan-4-yl)-
5-hydroxy-4-methylhexan-3-one 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.22(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.801(2)
_cell_length_b                   6.6536(8)
_cell_length_c                   13.944(3)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     1077.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7237
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3819
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0410P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                3470
_reflns_number_total             3819
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo9003635_si_001.cif
_cod_data_source_block           mahr32a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024540