Enantiopure 2-substituted glyceraldehyde derivatives by aza-Claisen rearrangement or C-alkylation of enamines.
Bridgwood, Katy L.; Tzschucke, C. Christoph; O'Brien, Matthew; Wittrock, Sven; Goodman, Jonathan M.; Davies, John E.; Logan, Angus W. J.; Hüttl, Matthias R M; Ley, Steven V.; Organic letters 10 (2008) 4537–4540; doi:10.1021/ol8018242

data_1504899
_publ_section_title
;
 Enantiopure 2-substituted glyceraldehyde derivatives by aza-Claisen
 rearrangement or C-alkylation of enamines.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4537
_journal_page_last               4540
_journal_paper_doi               10.1021/ol8018242
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration
;
 Flack parameter -0.004(7)
;
_chemical_formula_moiety         'C18 H32 N O4 +, Br -'
_chemical_formula_sum            'C18 H32 Br N O4'
_chemical_formula_weight         406.36
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 110.1510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9067(2)
_cell_length_b                   12.6246(3)
_cell_length_c                   10.7306(3)
_cell_measurement_reflns_used    6279
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      1.00
_cell_volume                     1005.55(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8633
_diffrn_reflns_theta_full        32.02
_diffrn_reflns_theta_max         32.02
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    2.064
_exptl_absorpt_correction_T_max  0.634
_exptl_absorpt_correction_T_min  0.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(7)
_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     222
_refine_ls_number_reflns         6265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0381P)^2^+0.2436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                5675
_reflns_number_total             6265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8018242_si_001.cif
_cod_data_source_block           sl0738
_cod_original_cell_volume        1005.55(4)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1504899