Enantioselective formal alpha-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction-Julia-Kocienski olefination sequence
Daisuke Uraguchi; Shinji Nakamura; Hitoshi Sasaki; Yuki Konakade; Takashi Ooi; Chem.Commun. 50 (2014) 3491–; doi:10.1039/C3CC49477B

data_7112111
_publ_section_title
;
 Enantioselective formal alpha-allylation of nitroalkanes through a chiral
 iminophosphorane-catalyzed Michael reaction-Julia-Kocienski olefination
 sequence
;
_journal_name_full               Chem.Commun.
_journal_page_first              3491
_journal_paper_doi               10.1039/C3CC49477B
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 N5 O4 S'
_chemical_formula_sum            'C17 H17 N5 O4 S'
_chemical_formula_weight         387.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.085(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.949(2)
_cell_length_b                   24.489(9)
_cell_length_c                   10.960(4)
_cell_measurement_reflns_used    5616
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      3.1416
_cell_volume                     1816.7(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device
;
Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14634
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.142
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8751
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7772
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0374P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                6174
_reflns_number_total             7772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc49477b3.cif
_cod_data_source_block           shelxs
_cod_original_cell_volume        1816.6(11)
_cod_database_code               7112111
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-3
_shelx_res_checksum              52450
_shelx_hkl_checksum              20931