Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with imines.
Shintani, Ryo; Murakami, Masataka; Hayashi, Tamio; Organic letters 11 (2009) 457–459; doi:10.1021/ol802569q

data_1503748
_publ_section_title
;
 Stereoselective synthesis of nipecotic acid derivatives via
 palladium-catalyzed decarboxylative cyclization of
 gamma-methylidene-delta-valerolactones with imines.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              457
_journal_page_last               459
_journal_paper_doi               10.1021/ol802569q
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C22 H28 N O5 P S'
_chemical_formula_weight         449.48
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.596(3)
_cell_length_b                   17.629(4)
_cell_length_c                   20.182(3)
_cell_measurement_reflns_used    31494
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     4481.5(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39914
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9519
_exptl_absorpt_correction_T_min  0.9291
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5132
_refine_ls_number_restraints     358
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+4.1851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                4246
_reflns_number_total             5132
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802569q_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        4481.2(16)
_cod_database_code               1503748