Pyrrolidine and Piperidine Formation via Copper(II) Carboxylate-Promoted Intramolecular Carboamination of Unactivated Olefins: Diastereoselectivity and Mechanism
Eric S. Sherman; Peter H. Fuller; Dhanalakshmi Kasi; Sherry R. Chemler; Journal of Organic Chemistry 72 (2007) 3896–3905; doi:10.1021/jo070321u

data_4022935
_publ_contact_author_address
;
Department of Chemistry
State University of New York at Buffalo
Buffalo, NY
14260-3000, USA
;
_publ_contact_author_email       mm278@buffalo.edu
_publ_contact_author_name        'Marc Messerschmidt'
_publ_contact_author_phone       (716)645-6800x2233
_publ_section_title
;
 Pyrrolidine and Piperidine Formation via Copper(II)
 Carboxylate-Promoted Intramolecular Carboamination of Unactivated
 Olefins: Diastereoselectivity and Mechanism
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3896
_journal_page_last               3905
_journal_paper_doi               10.1021/jo070321u
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C19 H27 N O2 S'
_chemical_formula_sum            'C19 H27 N O2 S'
_chemical_formula_weight         333.48
_chemical_name_systematic
; 
 1-Cyclohexylmethyl-8-methyl-2,3,10,10a-tetrahydro-1H-pyrrolo[1,2-b]
[1,2]benzothiazine 5,5-dioxide 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.547(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0885(13)
_cell_length_b                   6.3626(8)
_cell_length_c                   25.563(3)
_cell_measurement_reflns_used    3145
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      3.25
_cell_volume                     1773.1(4)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX2'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            19665
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        'not measured'
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.8392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2004/1; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+1.0728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                3253
_reflns_number_total             4246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070321usi20070216_012116.cif
_cod_data_source_block           p21n
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022935