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_1546004
_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_formula_moiety         'C21 H33 N O6'
_chemical_formula_sum            'C21 H33 N O6'
_chemical_formula_weight         395.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-15
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5273)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 91.716(4)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   5.7733(2)
_cell_length_b                   9.1531(4)
_cell_length_c                   41.7797(19)
_cell_measurement_reflns_used    3276
_cell_measurement_temperature    123
_cell_measurement_theta_max      75.2095
_cell_measurement_theta_min      3.1721
_cell_volume                     2206.80(16)
_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
;
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)
;
_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    'SIR97 (Burla et al., 2007)'
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 10.3546
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details
;
  1 omega  -96.00  -12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2064  125.0000  150.0000 84

  2 omega -112.00  -60.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2064  -37.0000   60.0000 52

  3 omega -114.00  -20.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2064  -37.0000  -30.0000 94

  4 omega   46.00  146.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  179.0000  -60.0000 100

  5 omega   45.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591 -105.0000    0.0000 66

  6 omega   96.00  131.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591   45.0000  -30.0000 35

  7 omega   46.00   71.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -45.0000 -180.0000 25

  8 omega   43.00   70.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -45.0000  -30.0000 27

  9 omega   36.00   76.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  -45.0000 -120.0000 40

 10 omega   43.00  126.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  179.0000  150.0000 83

 11 omega   80.00  146.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5591  111.0000 -120.0000 66
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0385874000
_diffrn_orient_matrix_UB_12      0.1293780000
_diffrn_orient_matrix_UB_13      -0.0227884000
_diffrn_orient_matrix_UB_21      0.0495414000
_diffrn_orient_matrix_UB_22      -0.1073994000
_diffrn_orient_matrix_UB_23      -0.0273711000
_diffrn_orient_matrix_UB_31      -0.2596078000
_diffrn_orient_matrix_UB_32      -0.0011883000
_diffrn_orient_matrix_UB_33      -0.0096675000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            8423
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.390
_diffrn_reflns_theta_min         4.235
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
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
            model based on expressions derived by R.C. Clark & J.S. Reid.
(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    1.190
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       'flat rod'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3002
_exptl_crystal_size_mid          0.1264
_exptl_crystal_size_min          0.0446
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0900P)^2^+0.1950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3769
_reflns_number_total             4381
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01111_si_003.cif
_cod_data_source_block           k165
_cod_depositor_comments
'Adding full bibliography for 1546004--1546006.cif.'
_cod_original_cell_volume        2206.8(3)
_cod_database_code               1546004
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c21 h30 o6 n'
_cell_oxdiff_angle_alpha         90.027(5)
_cell_oxdiff_angle_beta          91.595(6)
_cell_oxdiff_angle_gamma         89.974(6)
_cell_oxdiff_length_a            5.7701(5)
_cell_oxdiff_length_b            9.1618(6)
_cell_oxdiff_length_c            41.761(2)
_cell_oxdiff_measurement_reflns_used 3276
_cell_oxdiff_volume              2206.8(3)
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
;
_shelx_res_checksum              67296
_shelx_hkl_checksum              50255
_olex2_date_sample_completion    2011-08-05
_olex2_date_sample_data_collection 2011-08-05
_olex2_date_sample_submission    2011-07-22
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_submission_original_sample_id K165
_olex2_submission_special_instructions 'No special instructions were received'