Asymmetric synthesis of (-)-sedacryptine through a diastereoselective Mannich reaction of N,O-acetals with ketones.
Liu, Yi-Wen; Ma, Rui-Jun; Yan, Jia-Hang; Zhou, Zhu; Wei, Bang-Guo; Organic & biomolecular chemistry 16 (2018) 771–779; doi:10.1039/c7ob02989f

data_7156046
_publ_section_title
;
 Asymmetric synthesis of (-)-sedacryptine through a diastereoselective
 Mannich reaction of N,O-acetals with ketones.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              771
_journal_page_last               779
_journal_paper_doi               10.1039/c7ob02989f
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H23 N O2'
_chemical_formula_weight         237.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-11-14 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7672(2)
_cell_length_b                   9.3611(3)
_cell_length_c                   19.2665(6)
_cell_measurement_reflns_used    4647
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      140.056
_cell_measurement_theta_min      11.392
_cell_volume                     1400.86(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8103
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.077
_diffrn_reflns_theta_min         6.594
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
; 
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.16(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.1350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2410
_reflns_number_total             2596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02989f2.cif
_cod_data_source_block           cu_d8v17582_0m
_cod_depositor_comments
'Adding full bibliography for 7156046--7156047.cif.'
_cod_database_code               7156046
_shelx_estimated_absorpt_t_min   0.902
_shelx_estimated_absorpt_t_max   0.933
_shelxl_version_number           2013-4
_shelx_res_checksum              67784