A highly enantioselective, organocatalytic [3+2]-cycloannulation reaction towards the de novo-synthesis of 1-cyclopentenyl-alpha-keto esters
Pradeep R. Nareddy; Christoph Schneider; Chem.Commun. 51 (2015) 14797–; doi:10.1039/C5cc05967D

data_7117832
_publ_section_title
;
 A highly enantioselective, organocatalytic [3+2]-cycloannulation reaction
 towards the de novo-synthesis of 1-cyclopentenyl-alpha-keto esters
;
_journal_name_full               Chem.Commun.
_journal_page_first              14797
_journal_paper_doi               10.1039/C5cc05967D
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H21 Br O3'
_chemical_formula_weight         365.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-20T13:19:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-07-14 deposited with the CCDC.
2015-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.448(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2717(2)
_cell_length_b                   5.63430(10)
_cell_length_c                   15.8631(3)
_cell_measurement_reflns_used    5102
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      30.629
_cell_measurement_theta_min      2.227
_cell_volume                     814.94(3)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
;
_computing_publication_material
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
;
 SHELXS-2013
 Program for Crystal Structure Analysis (Release 2013-1)
 G. M. Sheldrick, Instit\"ut f\"ur Anorganische Chemie der Universit\"at,
 Tammanstrasse 4, D-3400 G\"ottingen, Germany.
 G. M. Sheldrick, Acta. Cryst., 2008, A64, 112 - 122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.356
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0191587
_diffrn_orient_matrix_UB_12      -0.0081677
_diffrn_orient_matrix_UB_13      0.0412404
_diffrn_orient_matrix_UB_21      -0.0738926
_diffrn_orient_matrix_UB_22      -0.0229873
_diffrn_orient_matrix_UB_23      -0.0191615
_diffrn_orient_matrix_UB_31      0.0149829
_diffrn_orient_matrix_UB_32      -0.1234383
_diffrn_orient_matrix_UB_33      0.0008524
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13344
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         32.343
_diffrn_reflns_theta_min         2.234
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.532
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.80872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.68
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1749 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(4)
_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     283
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0252P)^2^+0.2232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                4523
_reflns_number_total             5337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05967d2.cif.txt
_cod_data_source_block           x2266fin
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7117832