Highly Effective Vinylogous Mukaiyama-Michael Reaction Catalyzed by Silyl Methide Species Generated from 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane
Arata Takahashi; Hikaru Yanai; Min Zhang; Takaaki Sonoda; Masaaki Mishima; Takeo Taguchi; Journal of Organic Chemistry 75 (2010) 1259–1265; doi:10.1021/jo902641g

data_4025252
_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@ps.toyaku.ac.jp
_publ_contact_author_name        'Hikaru Yanai'
_publ_section_title
;
 Highly Effective Vinylogous Mukaiyama-Michael Reaction Catalyzed by Silyl
 Methide Species Generated from
 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1259
_journal_page_last               1265
_journal_paper_doi               10.1021/jo902641g
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C17 H25 Br O3'
_chemical_formula_sum            'C17 H25 Br O3'
_chemical_formula_weight         357.28
_chemical_name_systematic
; 
(S*)-3-bromo-5-((R*)-1-cyclohexyl-4,4-dimethyl-3-oxopentyl)-5H-furan-2-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             '13 February 2009'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.780(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.477(3)
_cell_length_b                   10.226(3)
_cell_length_c                   17.617(5)
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.32
_cell_volume                     1703.6(9)
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9346
_diffrn_reflns_theta_full        27.69
_diffrn_reflns_theta_max         27.69
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    2.420
_exptl_absorpt_correction_T_max  0.9094
_exptl_absorpt_correction_T_min  0.6060
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0492P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3238
_reflns_number_total             3894
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902641g_si_005.cif
_cod_data_source_block           anti-3je
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4025252