Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via Cu(I)-catalyzed reductive aldol cyclization.
Lam, Hon Wai; Murray, Gordon J.; Firth, James D.; Organic letters 7 (2005) 5743–5746; doi:10.1021/ol052599j

data_1506780
_publ_section_title
;
 Diastereoselective synthesis of 4-hydroxypiperidin-2-ones via
 Cu(I)-catalyzed reductive aldol cyclization.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              5743
_journal_page_last               5746
_journal_paper_doi               10.1021/ol052599j
_journal_volume                  7
_journal_year                    2005
_chemical_compound_source        'Hon Lam. No reaction number given.'
_chemical_formula_moiety         'C14 H19 N1 O3'
_chemical_formula_sum            'C14 H19 N O3'
_chemical_formula_weight         249.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.4690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3947(2)
_cell_length_b                   9.4295(2)
_cell_length_c                   21.4180(5)
_cell_measurement_reflns_used    5061
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2
_cell_volume                     1283.26(6)
_computing_cell_refinement       Saint
_computing_data_collection       Smart
_computing_data_reduction        Saint
_computing_molecular_graphics    XP
_computing_publication_material  'XCIF, PLATON, ENCIFER'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'Omega and phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19679
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         1.91
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs v 2004/1'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method 'From CDCl3.'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.3806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                3108
_reflns_number_total             3726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052599jsi20051027_065602.cif
_cod_data_source_block           hlme0h
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multiscan' changed to
'multi-scan' 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      'P 21/c'
_cod_database_code               1506780