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_1505663
_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 rmad
_chemical_formula_moiety         'C14 H25 N O5 Si'
_chemical_formula_sum            'C14 H25 N O5 Si'
_chemical_formula_weight         315.44
_chemical_melting_point          326.7(15)
_chemical_name_common            ozonide
_chemical_name_systematic
; [(1R,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-
methoxy-4-methyl-2,3,7-trioxa-bicyclo[2.2.1]hept-1-yl]-
acetonitrile  
;
_chemical_optical_rotation       '[\a]~D~^23^=-23.3 (c=0.43, 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                 115.27(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.726(1)
_cell_length_b                   8.1169(5)
_cell_length_c                   11.027(1)
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      2.22
_cell_volume                     868.16(14)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_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 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Siemens SMART 1K 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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11173
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         2.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(63)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4818
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0444P)^2^+0.0779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.83
_reflns_number_gt                4706
_reflns_number_total             4818
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol7025262-file002.cif
_cod_data_source_block           19
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '326.7(1.5)' was changed to
'326.7(15)' - precision was estimated.

'_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        868.16(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1505663