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_4025558
_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_formula_moiety         'C17 H29 Br O3 Si'
_chemical_formula_sum            'C17 H29 Br O3 Si'
_chemical_formula_weight         389.40
_chemical_melting_point          47.7
_chemical_name_systematic
; 
(S*)-4-Bromo-5-((1R*,2S*)-1-(tert-butyldimethylsilyloxy)-
2-methylcyclohexyl)furan-2(5H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '28 April 09'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.1770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1308(13)
_cell_length_b                   8.9024(7)
_cell_length_c                   14.1885(11)
_cell_measurement_reflns_used    5261
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.65
_cell_volume                     1912.5(3)
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10646
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_T_max  0.5853
_exptl_absorpt_correction_T_min  0.5102
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.7023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                3846
_reflns_number_total             4337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100915e_si_004.cif
_cod_data_source_block           3g-Si-maj
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025558