Asymmetric, anti-selective scandium-catalyzed Sakurai additions to glyoxyamide. Applications to the syntheses of N-boc D-alloisoleucine and D-isoleucine.
Evans, David A.; Aye, Yimon; Wu, Jimmy; Organic letters 8 (2006) 2071–2073; doi:10.1021/ol0604771

data_1505947
_publ_section_title
;
 Asymmetric, anti-selective scandium-catalyzed Sakurai additions to
 glyoxyamide. Applications to the syntheses of N-boc D-alloisoleucine and
 D-isoleucine.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2071
_journal_page_last               2073
_journal_paper_doi               10.1021/ol0604771
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4101(17)
_cell_length_b                   8.6372(18)
_cell_length_c                   20.288(4)
_cell_measurement_temperature    273(2)
_cell_volume                     1473.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6355
_diffrn_reflns_theta_full        22.49
_diffrn_reflns_theta_max         22.49
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.398
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         1922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.398
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0954
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+2.4041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                1862
_reflns_number_total             1922
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0604771si20060224_113459.cif
_cod_data_source_block           sad
_cod_database_code               1505947