A Highly Stereoselective Diels–Alder Cycloaddition of Enones with Chiral Cyclic 2-Amidodienes Derived from Allenamides
Fang, Li-Chao; Hsung, Richard P.; Ma, Zhi-Xiong; Presser, William R.; Organic Letters 15 (2013) 4842–; doi:10.1021/ol402254p

data_1512348
_publ_section_title
;
 A Highly Stereoselective Diels--Alder Cycloaddition of Enones with Chiral
 Cyclic 2-Amidodienes Derived from Allenamides
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              4842
_journal_paper_doi               10.1021/ol402254p
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H24 N2 O5'
_chemical_formula_sum            'C21 H24 N2 O5'
_chemical_formula_weight         384.42
_chemical_name_common            130125a
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3046(7)
_cell_length_b                   26.6589(16)
_cell_length_c                   6.2333(4)
_cell_measurement_reflns_used    2924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.05
_cell_measurement_theta_min      3.32
_cell_volume                     1878.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-100 Kappa'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_number            14731
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.103
_diffrn_reflns_theta_min         3.315
_diffrn_source                   'Cu microsoure'
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.9287
_exptl_absorpt_correction_T_min  0.8178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       Plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.5954P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3187
_reflns_number_total             3404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol402254p_si_005.cif
_cod_data_source_block           13125a
_cod_database_code               1512348
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2013-2
_shelx_res_checksum              1018
_shelx_hkl_checksum              66964