Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres.
Nairoukh, Zackaria; Kumar, Gunda G K S Narayana; Minko, Yury; Marek, Ilan; Chemical science 8 (2017) 627–630; doi:10.1039/c6sc03036j

data_1544138
_publ_section_title
;
 Enantioselective allylic alkylation of stereodefined polysubstituted
 copper enolates as an entry to acyclic quaternary carbon stereocentres.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              627
_journal_page_last               630
_journal_paper_doi               10.1039/c6sc03036j
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C28 H33 N O5'
_chemical_formula_sum            'C28 H33 N O5'
_chemical_formula_weight         463.55
_chemical_melting_point          329.15
_chemical_name_common            'Marek99 (Zack)'
_chemical_name_systematic
'Benzyl (S)-4-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-methyl-2-methyleneoctanoate '
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-06-28 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.003(6)
_cell_length_b                   14.84(3)
_cell_length_c                   28.93(3)
_cell_measurement_reflns_used    2168
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      0.7
_cell_volume                     2577(6)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Mercury 3.5'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-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  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2210
_diffrn_reflns_theta_full        24.14
_diffrn_reflns_theta_max         24.14
_diffrn_reflns_theta_min         1.41
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9655
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'   
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0
_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     309
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0460
_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^)+(0.1044P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                1814
_reflns_number_total             2210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6sc03036j2.cif
_cod_data_source_block           Marek99
_cod_depositor_comments
;Adding full bibliography for 1544138.cif.

 Adding full bibliography for 1544138.cif.
;
_cod_original_cell_volume        2577(7)
_cod_database_code               1544138
_solvent_exptl_crystal_recrystallization_method 'Hexane and ethyl acetate'