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_1504901
_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
;
 2227 Friedel pairs were averaged for the refinement
;
_chemical_formula_moiety         'C16 H22 O5'
_chemical_formula_sum            'C16 H22 O5'
_chemical_formula_weight         294.34
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.424(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.3552(4)
_cell_length_b                   6.7979(2)
_cell_length_c                   11.9364(3)
_cell_measurement_reflns_used    5678
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      34.97
_cell_measurement_theta_min      1.02
_cell_volume                     1610.11(7)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9452
_diffrn_reflns_theta_full        34.98
_diffrn_reflns_theta_max         34.98
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.951
_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    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+0.6255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                3161
_reflns_number_total             3713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8018242_si_003.cif
_cod_data_source_block           sl0818
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1504901