Thio-Claisen Rearrangement Used in Preparing Anti-β-Functionalized γ,δ-Unsaturated Amino Acids: Scope and Limitations
Zhihua Liu; Sukeshi J. Mehta; Kwang-Soo Lee; Bryan Grossman; Hongchang Qu; Xuyuan Gu; Gary S. Nichol; Victor J. Hruby; Journal of Organic Chemistry 77 (2012) 1289–1300; doi:10.1021/jo201753q

data_4026913
_publ_section_title
;
 Thio-Claisen Rearrangement Used in Preparing Anti-\b-Functionalized
 \g,\d-Unsaturated Amino Acids: Scope and Limitations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1289
_journal_page_last               1300
_journal_paper_doi               10.1021/jo201753q
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H34 N2 O2 S'
_chemical_formula_sum            'C27 H34 N2 O2 S'
_chemical_formula_weight         450.62
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.889(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.913(11)
_cell_length_b                   6.478(4)
_cell_length_c                   22.834(13)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.30
_cell_measurement_theta_min      2.41
_cell_volume                     2614(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2004)'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2001)'
_computing_structure_solution    'SIR92 (Altomare et al., 1992)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_sigmaI/netI    0.1291
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8327
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 2007'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881. 2081 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(16)
_refine_ls_extinction_coef       0.0129(15)
_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   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4553
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0660
_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^)+(0.0872P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1939
_reflns_number_gt                2704
_reflns_number_total             4553
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo201753q_si_001.cif
_cod_data_source_block           vjh104
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4026913