Hetero-Diels-Alder reactions of cyclic ketone derived enamide. A new and efficient concept for the asymmetric Robinson annulation.
Gallier, Florian; Hussain, Hidayat; Martel, Arnaud; Kirschning, Andreas; Dujardin, Gilles; Organic letters 11 (2009) 3060–3063; doi:10.1021/ol901065e

data_1504004
_publ_section_title
;
 Hetero-Diels-Alder reactions of cyclic ketone derived enamide. A new and
 efficient concept for the asymmetric Robinson annulation.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3060
_journal_page_last               3063
_journal_paper_doi               10.1021/ol901065e
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H27 N O5'
_chemical_formula_sum            'C22 H27 N O5'
_chemical_formula_weight         385.45
_chemical_melting_point          388
_chemical_name_common            endo-6a
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2009-05-07 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.82(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.082(7)
_cell_length_b                   11.525(15)
_cell_length_c                   10.141(8)
_cell_measurement_pressure       101.3
_cell_measurement_reflns_used    7427
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     1026.1(18)
_computing_cell_refinement       'STADI4 v1.07 (Stoe,1998)'
_computing_data_collection       'STADI4 v1.07 (Stoe,1998)'
_computing_data_reduction        'X-RED v1.10 (Stoe,1998)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'ENCIFER v1.2 (CCDC, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SIEMENS AED2'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0866
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7409
_diffrn_reflns_theta_full        32.48
_diffrn_reflns_theta_max         32.48
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       parallepiped
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         7409
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.2160
_refine_ls_R_factor_gt           0.0772
_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^)+(0.0733P)^2^+0.2346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.2062
_reflns_number_gt                2996
_reflns_number_total             7409
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol901065e_si_003.cif
_cod_data_source_block           6a
_cod_depositor_comments
;
The following automatic conversions were performed:
'__computing_data_collection' tag replaced with
'_computing_data_collection'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_database_code               1504004