Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters.
Cailleau, Thaïs; Cooke, Jason W. B.; Davies, Stephen G.; Ling, Kenneth B.; Naylor, Alan; Nicholson, Rebecca L.; Price, Paul D.; Roberts, Paul M.; Russell, Angela J.; Smith, Andrew D.; Thomson, James E.; Organic & biomolecular chemistry 5 (2007) 3922–3931; doi:10.1039/b712937h

data_7151190
_publ_section_title
;
 Asymmetric synthesis of
 beta-amino-gamma-substituted-gamma-butyrolactones: double
 diastereoselective conjugate addition of homochiral lithium amides to
 homochiral alpha,beta-unsaturated esters.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3922
_journal_page_last               3931
_journal_paper_doi               10.1039/b712937h
_journal_volume                  5
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C36 H51 N1 O3 Si1'
_chemical_formula_sum            'C36 H51 N O3 Si'
_chemical_formula_weight         573.89
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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_date             06-08-25
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                71.9010(6)
_cell_angle_beta                 67.6483(7)
_cell_angle_gamma                76.2070(8)
_cell_formula_units_Z            2
_cell_length_a                   11.4449(2)
_cell_length_b                   11.8000(2)
_cell_length_c                   14.6478(2)
_cell_measurement_reflns_used    7262
_cell_measurement_temperature    190
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1722.68(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT. Nonius (1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'USER DEFINED STRUCTURE SOLUTION'
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14183
_diffrn_reflns_theta_full        26.457
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         5.175
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.96
_refine_diff_density_min         -0.87
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     739
_refine_ls_number_reflns         6098
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000874
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.13 0.753 0.606
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1030
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0822
_reflns_limit_h_max              14
_reflns_limit_h_min              -13
_reflns_limit_k_max              15
_reflns_limit_k_min              -14
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                6098
_reflns_number_total             7805
_reflns_threshold_expression     I>2.00u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.924(2)
_oxford_structure_analysis_title '8250950 SGD155'
_cod_data_source_file            b712937h.txt
_cod_data_source_block           1
_cod_original_formula_sum        'C36 H51 N1 O3 Si1'
_cod_database_code               7151190
_refine_ls_r_factor_ref          0.0668
_reflns_number_all               7805