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_1506781
_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, reaction 1/35/2'
_chemical_formula_moiety         'C19 H21 N1 O3'
_chemical_formula_sum            'C19 H21 N O3'
_chemical_formula_weight         311.37
_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'
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_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 98.577(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.693(2)
_cell_length_b                   5.8798(7)
_cell_length_c                   13.1078(18)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     1577.0(3)
_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 0.994
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'Omega and phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
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_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.780
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_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method 'From CDCl3'
_exptl_crystal_size_max          0.70
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.2008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                3348
_reflns_number_total             4573
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052599jsi20051027_065618.cif
_cod_data_source_block           hl1352
_cod_depositor_comments
;
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 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geometric' was changed to
'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1506781