Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene N,O-Acetal with Acetals.
Sagawa, Naoya; Moriya, Hiroki; Hosokawa, Seijiro; Organic letters 19 (2017) 250–253; doi:10.1021/acs.orglett.6b03549

data_1544963
_publ_section_title
;
 Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene
 N,O-Acetal with Acetals.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              250
_journal_page_last               253
_journal_paper_doi               10.1021/acs.orglett.6b03549
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C16 H27 N O4'
_chemical_formula_sum            'C16 H27 N O4'
_chemical_formula_weight         297.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.684(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.8462(4)
_cell_length_b                   11.0660(5)
_cell_length_c                   10.6654(6)
_cell_measurement_reflns_used    5795
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.09
_cell_measurement_theta_min      4.00
_cell_volume                     854.40(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9776
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.163
_diffrn_reflns_theta_min         4.493
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324.00
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.40
_refine_ls_abs_structure_details
;
 Flack x determined using 582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0382P)^2^+1.5182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.2071
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                1677
_reflns_number_total             3006
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol6b03549_si_003.cif
_cod_data_source_block           20150619Moriya
_cod_depositor_comments          'Adding full bibliography for 1544963.cif.'
_cod_database_code               1544963
_shelxl_version_number           2014/6
_shelx_res_checksum              7528
_shelx_hkl_checksum              62045