Highly Efficient Synthesis of Azabicyclo[x.y.0]alkane Amino Acids and Congeners by Means of Rh-Catalyzed Cyclohydrocarbonylation
Wen-Hua Chiou; Nobihiro Mizutani; Iwao Ojima; Journal of Organic Chemistry 72 (2007) 1871–1882; doi:10.1021/jo061692y

data_4022611
_publ_section_title
;
 Highly Efficient Synthesis of Azabicyclo[x.y.0]alkane Amino Acids
 and Congeners by Means of Rh-Catalyzed Cyclohydrocarbonylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1871
_journal_page_last               1882
_journal_paper_doi               10.1021/jo061692y
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C13 H21 N2 O4'
_chemical_formula_weight         269.32
_chemical_melting_point          122
_chemical_name_common            (S,S,S)-5j
_chemical_name_systematic
; 
 (3S,6S,9S)-1-Aza-3-tert-butoxycarbonylamino-9-methyl-
 5-oxa-2-oxobicyclo[4.3.0]nonane  
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.780(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.050(8)
_cell_length_b                   6.229(5)
_cell_length_c                   12.106(9)
_cell_measurement_temperature    273(2)
_cell_volume                     741.9(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0762
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2813
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             290
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.1890
_refine_ls_R_factor_gt           0.1406
_refine_ls_shift/su_max          2.701
_refine_ls_shift/su_mean         0.092
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3364
_refine_ls_wR_factor_ref         0.3720
_reflns_number_gt                1032
_reflns_number_total             1926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061692ysi20060821_040150.cif
_cod_data_source_block           (S,S,S)-5j
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022611