Cyclopent-2-enylaluminium as allylzinc precursor for the diastereoselective allylmetallation of non-racemic imines: applications to the synthesis of enantiomerically enriched heterocycles.
Coffinet, Michaël; Lamy, Samantha; Jaroschik, Florian; Vasse, Jean-Luc; Organic & biomolecular chemistry 14 (2015) 69–73; doi:10.1039/c5ob02184g

data_7154792
_publ_section_title
;
 Cyclopent-2-enylaluminium as allylzinc precursor for the
 diastereoselective allylmetallation of non-racemic imines: applications
 to the synthesis of enantiomerically enriched heterocycles.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              69
_journal_page_last               73
_journal_paper_doi               10.1039/c5ob02184g
_journal_volume                  14
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H25 N O2'
_chemical_formula_weight         323.42
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-15 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(0)
_cell_angle_beta                 109.415(5)
_cell_angle_gamma                90.000(0)
_cell_formula_units_Z            2
_cell_length_a                   10.585(5)
_cell_length_b                   6.810(5)
_cell_length_c                   13.050(5)
_cell_measurement_reflns_used    9781
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.63
_cell_measurement_theta_min      3.59
_cell_volume                     887.2(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32896
_diffrn_reflns_theta_full        74.62
_diffrn_reflns_theta_max         74.62
_diffrn_reflns_theta_min         3.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.1390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0674
_reflns_number_gt                3527
_reflns_number_total             3628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02184g2.cif
_cod_data_source_block           cu_14jlv002_0m
_cod_depositor_comments
'Adding full bibliography for 7154791--7154792.cif.'
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7154792