A novel, efficient, diastereo- and enantioselective Mukaiyama aldol-based synthesis of a vinyl cyclopentanone core derivative of viridenomycin.
Batsanov, Andrei S.; Knowles, Jonathan P.; Lightfoot, Andrew P.; Maw, Graham; Thirsk, Carl E.; Twiddle, Steven J. R.; Whiting, Andrew; Organic letters 9 (2007) 5565–5568; doi:10.1021/ol7025262

data_1505662
_publ_section_title
;
 A novel, efficient, diastereo- and enantioselective Mukaiyama aldol-based
 synthesis of a vinyl cyclopentanone core derivative of viridenomycin.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              5565
_journal_page_last               5568
_journal_paper_doi               10.1021/ol7025262
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H29 N3 O7 Si'
_chemical_formula_sum            'C19 H29 N3 O7 Si'
_chemical_formula_weight         439.54
_chemical_melting_point          370.7(5)
_chemical_name_systematic
; N-2,4-Dinitrophenyl 3-(tert-butyldimethylsilyloxy|)-2-methoxy-4
-methylpent-4-enamide  
;
_chemical_optical_rotation       '[\a]~D~^23^=+104 (c=0.68, DCM)'
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.32(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.1833(12)
_cell_length_b                   6.6134(6)
_cell_length_c                   13.7973(12)
_cell_measurement_reflns_used    6994
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      33.32
_cell_measurement_theta_min      2.61
_cell_volume                     1135.19(19)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 6K CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15792
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(86)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         6620
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0598P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.85
_reflns_number_gt                5963
_reflns_number_total             6620
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol7025262-file002.cif
_cod_data_source_block           15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1135.2(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1505662