Stereopentads Derived from a Sequence of Mukaiyama Aldolization and Free Radical Reduction on α-Methyl-β-alkoxy Aldehydes: A General Strategy for Efficient Polypropionate Synthesis
Jean-François Brazeau; Philippe Mochirian; Michel Prévost; Yvan Guindon; Journal of Organic Chemistry 74 (2009) 64–74; doi:10.1021/jo8021583

data_4024243
_publ_contact_author
;
    Dr Yvan Guindon
    Institut de recherches cliniques de Montr\'eal
    110 ouest, Avenue des Pins
    Montr\'eal, Qu\'ebec
    Canada H2W 1R7
;
_publ_contact_author_email       guindoy@ircm.umontreal.ca
_publ_contact_author_fax         '514 987 5789'
_publ_contact_author_phone       '514 987 5786'
_publ_section_title
;
Stereopentads Derived from a Sequence of Mukaiyama Aldolization and Free
Radical Reduction on \a-Methyl-\b-alkoxy Aldehydes: A General Strategy for
Efficient Polypropionate Synthesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              64
_journal_page_last               74
_journal_paper_doi               10.1021/jo8021583
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'synthesized by the authors, see text'
_chemical_formula_moiety         'C10 H18 O4'
_chemical_formula_sum            'C10 H18 O4'
_chemical_formula_weight         202.244
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                83.301(3)
_cell_angle_beta                 86.487(3)
_cell_angle_gamma                69.316(2)
_cell_formula_units_Z            4
_cell_length_a                   8.6992(3)
_cell_length_b                   9.7549(4)
_cell_length_c                   13.8934(6)
_cell_measurement_reflns_used    1003
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.61
_cell_measurement_theta_min      4.87
_cell_volume                     1095.21(8)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.907
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker AXS SMART 2K/Platform'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14794
_diffrn_reflns_theta_full        71.86
_diffrn_reflns_theta_max         71.86
_diffrn_reflns_theta_min         3.20
_diffrn_standards_decay_%        'no decay, variation  0.0'
_diffrn_standards_number         89
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.9500
_exptl_absorpt_correction_T_min  0.1100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             440.0
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.931
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_restrained_S_obs      1.100
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0653P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1214
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2423
_reflns_number_total             3892
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo8021583_si_003.cif
_cod_data_source_block           guin22
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024243