Enantioselective Three-Step Synthesis of Homo-β-proline: A Donor-Acceptor Cyclopropane as Key Intermediate.
Pilsl, Ludwig K. A.; Ertl, Thomas; Reiser, Oliver; Organic letters 19 (2017) 2754–2757; doi:10.1021/acs.orglett.7b01111

data_1546005
_publ_section_title
;
 Enantioselective Three-Step Synthesis of Homo-\b-proline: A
 Donor-Acceptor Cyclopropane as Key Intermediate.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2754
_journal_page_last               2757
_journal_paper_doi               10.1021/acs.orglett.7b01111
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H23 N O4'
_chemical_formula_sum            'C15 H23 N O4'
_chemical_formula_weight         281.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2016-12-15
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Olex2 1.2-alpha
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4639(3)
_cell_length_b                   6.1799(2)
_cell_length_c                   13.1692(5)
_cell_measurement_reflns_used    1864
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.4161
_cell_measurement_theta_min      3.3532
_cell_volume                     770.21(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_details
;
  1 omega   63.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939   77.0000 -180.0000 48

  2 omega    3.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -125.0000   30.0000 94

  3 omega   56.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8939 -125.0000  -90.0000 28

  4 omega   37.00   74.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -45.0000   90.0000 37

  5 omega   80.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591 -120.0000   98.0000 27

  6 omega   87.00  156.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591   45.0000 -150.0000 69

  7 omega   55.00   83.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -98.0000  178.0000 28

  8 omega   39.00   68.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -45.0000  120.0000 29

  9 omega   80.00  157.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591   27.0000  -66.0000 77

 10 omega   14.00   41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2064   77.0000   90.0000 27

 11 omega   95.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2064   77.0000   90.0000 25

 12 omega   16.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2064   37.0000 -120.0000 37

 13 omega   42.00   74.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -45.0000    0.0000 32

 14 omega   35.00   61.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  179.0000  -90.0000 26

 15 omega  122.00  148.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  179.0000  -90.0000 26

 16 omega  130.00  156.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591   45.0000  120.0000 26

 17 omega   85.00  112.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591   45.0000  120.0000 27

 18 omega   36.00   61.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -45.0000 -120.0000 25

 19 omega   73.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -77.0000   60.0000 25

 20 omega  119.00  144.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -77.0000   60.0000 25

 21 omega   36.00   64.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -45.0000   30.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0937839000
_diffrn_orient_matrix_UB_12      -0.0741971000
_diffrn_orient_matrix_UB_13      -0.0890148000
_diffrn_orient_matrix_UB_21      -0.1218915000
_diffrn_orient_matrix_UB_22      0.0455325000
_diffrn_orient_matrix_UB_23      -0.0746591000
_diffrn_orient_matrix_UB_31      0.0534216000
_diffrn_orient_matrix_UB_32      0.2334884000
_diffrn_orient_matrix_UB_33      -0.0135580000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.940
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3296
_diffrn_reflns_point_group_measured_fraction_full 0.698
_diffrn_reflns_point_group_measured_fraction_max 0.670
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.646
_diffrn_reflns_theta_min         3.356
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.987
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
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(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.0264
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1026P)^2^+0.0459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1522
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_reflns_number_gt                2028
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_cod_data_source_file            ol7b01111_si_002.cif
_cod_data_source_block           k169
_cod_depositor_comments
'Adding full bibliography for 1546004--1546006.cif.'
_cod_database_code               1546005
_chemical_oxdiff_formula         'c34 h30 n2 o2'
_reflns_odcompleteness_completeness 93.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
;
_shelx_res_checksum              96847
_shelx_hkl_checksum              84983
_shelx_shelxl_version_number     2016/6
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 700'
_olex2_submission_special_instructions 'No special instructions were received'