Stereoselective Synthesis of α-Alkyl-β-keto Imides via Asymmetric Redox C-C Bond Formation between α-Alkyl-α-diazocarbonyl Compounds and Aldehydes
Takuya Hashimoto; Hisashi Miyamoto; Yuki Naganawa; Keiji Maruoka; Journal of the American Chemical Society 131 (2009) 11280–11281; doi:10.1021/ja903500w

data_4104868
_publ_contact_author_email       maruoka@kuchem.kyoto-u.ac.jp
_publ_contact_author_fax         +81(75)-753-4041
_publ_contact_author_name        'Keiji Maruoka'
_publ_contact_author_phone       +81(75)-753-4041
_publ_section_title
;
 Stereoselective Synthesis of \a-Alkyl-\b-keto Imides via Asymmetric Redox
 C-C Bond Formation between \a-Alkyl-\a-diazocarbonyl Compounds and
 Aldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11280
_journal_page_last               11281
_journal_paper_doi               10.1021/ja903500w
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H19 N3 O3 S '
_chemical_formula_sum            'C13 H19 N3 O3 S'
_chemical_formula_weight         297.37
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2009-01-07
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.58410(12)
_cell_length_b                   11.8140(2)
_cell_length_c                   18.4736(3)
_cell_measurement_reflns_used    14952
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.7
_cell_volume                     1436.96(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14988
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_exptl_absorpt_coefficient_mu    2.111
_exptl_absorpt_correction_T_max  0.531
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             632.00
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.44
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1083 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.004(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2629
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0458P)^2^+0.1567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2551
_reflns_number_total             2629
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja903500w_si_002.cif
_cod_data_source_block           '_hashimoto9105'
_cod_original_cell_volume        1436.96(5)
_cod_original_formula_sum        'C13 H19 N3 O3 S '
_cod_database_code               4104868