Syn-selective Kobayashi aldol reaction using the E,E-vinylketene silyl N,O-acetal.
Mukaeda, Yuki; Kato, Takuya; Hosokawa, Seijiro; Organic letters 14 (2012) 5298–5301; doi:10.1021/ol3024677

data_1508693
_publ_section_title
;
 Syn-selective Kobayashi aldol reaction using the E,E-vinylketene silyl
 N,O-acetal.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5298
_journal_page_last               5301
_journal_paper_doi               10.1021/ol3024677
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 N2 O6'
_chemical_formula_sum            'C19 H24 N2 O6'
_chemical_formula_weight         376.41
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.4055(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   24.9420(5)
_cell_length_b                   6.13836(11)
_cell_length_c                   12.4356(3)
_cell_measurement_reflns_used    9657
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      3.58
_cell_volume                     1888.05(7)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0370
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9796
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.780
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.320
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1337 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3235
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.9119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                3036
_reflns_number_total             3235
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol3024677_si_003.cif
_cod_data_source_block           4-nitrobenzaldehyde
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1888.04(6)
_cod_database_code               1508693