A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via the Kinugasa reaction employing ynamides.
Zhang, Xuejun; Hsung, Richard P.; Li, Hongyan; Zhang, Yu; Johnson, Whitney L.; Figueroa, Ruth; Organic letters 10 (2008) 3477–3479; doi:10.1021/ol801257j

data_1504796
_publ_section_title
;
 A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via
 the Kinugasa reaction employing ynamides.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3477
_journal_page_last               3479
_journal_paper_doi               10.1021/ol801257j
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H22 N2 O3'
_chemical_formula_sum            'C25 H22 N2 O3'
_chemical_formula_weight         398.45
_chemical_name_common            07094
_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                 114.730(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.950(2)
_cell_length_b                   5.8187(9)
_cell_length_c                   14.737(2)
_cell_measurement_reflns_used    1454
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      23.89
_cell_measurement_theta_min      2.74
_cell_volume                     1008.6(3)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6714
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
'Flack H D (1983), 1531 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         1965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                1479
_reflns_number_total             1965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801257j-file005.cif
_cod_data_source_block           07094
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1504796