Diethyl Phosphite Initiated Coupling of α-Ketoesters with Imines for Synthesis of α-Phosphonyloxy-β-amino Acid Derivatives and Aziridine-2-carboxylates.
Jiang, Jin; Liu, Hui; Lu, Chong-Dao; Xu, Yan-Jun; Organic letters 18 (2016) 880–883; doi:10.1021/acs.orglett.6b00273

data_1542664
_publ_section_title
;
 Diethyl Phosphite Initiated Coupling of \a-Ketoesters with Imines for
 Synthesis of \a-Phosphonyloxy-\b-amino Acid Derivatives and
 Aziridine-2-carboxylates.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              880
_journal_page_last               883
_journal_paper_doi               10.1021/acs.orglett.6b00273
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C29 H36 N O9 P S'
_chemical_formula_sum            'C29 H36 N O9 P S'
_chemical_formula_weight         605.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.369(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.580(6)
_cell_length_b                   10.731(4)
_cell_length_c                   17.820(7)
_cell_measurement_reflns_used    2399
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.973
_cell_measurement_theta_min      2.235
_cell_volume                     3071(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0497
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18108
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.418
_diffrn_reflns_theta_min         2.235
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0990 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.9119.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       bolock
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         6891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0605P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3972
_reflns_number_total             6891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00273_si_002.cif
_cod_data_source_block           7m
_cod_database_code               1542664
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C38(H38A,H38B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C31(H31), C33(H33), C34(H34)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,
 H37C), C39(H39A,H39B,H39C)
;
_olex2_submission_special_instructions 'No special instructions were received'