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_4108781
_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         'C45 H49 Cl N O5 P Pd '
_chemical_formula_sum            'C45 H49 Cl N O5 P Pd'
_chemical_formula_weight         856.71
_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             2008-08-19
_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                   8.0654(16)
_cell_length_b                   20.143(3)
_cell_length_c                   24.741(4)
_cell_measurement_reflns_used    36953
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     4019.5(12)
_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    SHELXS97
_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  0.048
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            38773
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       prism
_exptl_crystal_F_000             1776.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.04
_refine_diff_density_min         -1.59
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  4056 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     488
_refine_ls_number_reflns         9216
_refine_ls_R_factor_gt           0.0741
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0000P)^2^+21.3064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                8634
_reflns_number_total             9216
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja807662b_si_003.cif
_cod_data_source_block           '_80818yuki'
_cod_original_cell_volume        4019.6(12)
_cod_original_formula_sum        'C45 H49 Cl N O5 P Pd '
_cod_database_code               4108781