Palladium-Catalyzed Asymmetric Decarboxylative Lactamization of γ-Methylidene-δ-valerolactones with Isocyanates: Conversion of Racemic Lactones to Enantioenriched Lactams
Ryo Shintani; Soyoung Park; Fumitaka Shirozu; Masataka Murakami; Tamio Hayashi; Journal of the American Chemical Society 130 (2008) 16174–16175; doi:10.1021/ja807662b

data_4108780
_publ_section_title
;
 Palladium-Catalyzed Asymmetric Decarboxylative Lactamization of
 \g-Methylidene-\d-valerolactones with Isocyanates: Conversion of Racemic
 Lactones to Enantioenriched Lactams
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16174
_journal_page_last               16175
_journal_paper_doi               10.1021/ja807662b
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C23 H24 Cl N O3 '
_chemical_formula_sum            'C23 H24 Cl N O3'
_chemical_formula_weight         397.90
_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             2008-04-28
_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                   8.5610(19)
_cell_length_b                   11.733(4)
_cell_length_c                   20.575(6)
_cell_measurement_reflns_used    18253
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2066.7(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20155
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prism
_exptl_crystal_F_000             840.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         2.36
_refine_diff_density_min         -2.28
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2035 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.837
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     278
_refine_ls_number_reflns         17660
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
'w = 1/[0.0010Fo^2^ + 3.0000\s(Fo^2^) + 0.5000]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0519
_reflns_number_gt                17595
_reflns_number_total             4725
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja807662b_si_002.cif
_cod_data_source_block           '_80426yuki'
_cod_original_formula_sum        'C23 H24 Cl N O3 '
_cod_database_code               4108780