Enantioselective Intramolecular Michael Addition of Nitronates onto Conjugated Esters: Access to Cyclic γ-Amino Acids with up to Three Stereocenters
William J. Nodes; David R. Nutt; Ann M. Chippindale; Alexander J. A. Cobb; Journal of the American Chemical Society 131 (2009) 16016–16017; doi:10.1021/ja9070915

data_4105326
_publ_contact_author_address
; 
Reading School of Pharmacy
University or Reading
Whiteknights
Reading, Berks, UK RG6 6AP 
;
_publ_contact_author_email       a.j.a.cobb@rdg.ac.uk
_publ_contact_author_fax         '+44 118 3784703'
_publ_contact_author_name        'A.J.A. Cobb'
_publ_contact_author_phone       '+44 118 3784638'
_publ_section_title
;
 Enantioselective Intramolecular Michael Addition of Nitronates onto
 Conjugated Esters: Access to Cyclic \g-Amino Acids with up to Three
 Stereocenters
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16016
_journal_page_last               16017
_journal_paper_doi               10.1021/ja9070915
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H15 N1 O1'
_chemical_formula_sum            'C9 H15 N O'
_chemical_formula_weight         153.22
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-08-12
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 99.050(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3337(3)
_cell_length_b                   8.4781(5)
_cell_length_c                   10.0357(6)
_cell_measurement_reflns_used    2180
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      65
_cell_measurement_theta_min      5
_cell_volume                     448.16(5)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2008)'
_computing_data_collection       'Crystalis CCD, (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra CCD'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2188
_diffrn_reflns_theta_full        65.622
_diffrn_reflns_theta_max         65.622
_diffrn_reflns_theta_min         4.461
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
empirical absorption correction using CrysAlis RED
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_description       block
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983), 550 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0550
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1294
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.000168
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 7.59 -1.72 5.07 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0377
_refine_ls_wR_factor_gt          0.0376
_refine_ls_wR_factor_ref         0.0376
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1294
_reflns_number_total             1388
_reflns_threshold_expression     I>3.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          25.04(6)
_oxford_structure_analysis_title 'exp_2160 in P2(1)'
_cod_data_source_file            ja9070915_si_001.cif
_cod_data_source_block           CRYSTALS_cif
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C9 H15 N1 O1'
_cod_database_code               4105326