Carbon Acid Induced Mukaiyama Aldol Type Reaction of Sterically Hindered Ketones
Hikaru Yanai; Yasuhiro Yoshino; Arata Takahashi; Takeo Taguchi; Journal of Organic Chemistry 75 (2010) 5375–5378; doi:10.1021/jo100915e

data_4025557
_publ_contact_author_address
;
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences,
1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
;
_publ_contact_author_email       yanai@toyaku.ac.jp
_publ_contact_author_name        'Hikaru Yanai'
_publ_section_title
;
 Carbon Acid Induced Mukaiyama Aldol Type Reaction of Sterically Hindered
 Ketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5375
_journal_page_last               5378
_journal_paper_doi               10.1021/jo100915e
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H28 O3 S Si'
_chemical_formula_sum            'C16 H28 O3 S Si'
_chemical_formula_weight         328.53
_chemical_melting_point          95.2
_chemical_name_systematic
; 
(R*)-5-((3R*,4R*)-4-(tert-butyldimethylsilyloxy)-
3-methyltetrahydro-2H-thiopyran-4-yl)furan-2(5H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '03 Mar 10'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.5640(10)
_cell_angle_beta                 92.9930(10)
_cell_angle_gamma                99.9130(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8568(9)
_cell_length_b                   9.3124(10)
_cell_length_c                   12.7551(14)
_cell_measurement_temperature    90
_cell_volume                     912.71(17)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10625
_diffrn_reflns_theta_full        27.67
_diffrn_reflns_theta_max         27.67
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            Cololess
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     580
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0419P)^2^+0.2818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                3590
_reflns_number_total             4160
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100915e_si_003.cif
_cod_data_source_block           3e-Si-maj
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025557