Enantioselective Formal Aza-Diels-Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas
Mathieu P. Lalonde; Meredeth A. McGowan; Naomi S. Rajapaksa; Eric N. Jacobsen; Journal of the American Chemical Society 135 (2013) 1891–1894; doi:10.1021/ja310718f

data_4119266
_publ_section_title
;
 Enantioselective Formal Aza-Diels-Alder Reactions of Enones with Cyclic
 Imines Catalyzed by Primary Aminothioureas
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1891
_journal_page_last               1894
_journal_paper_doi               10.1021/ja310718f
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C28 H25 Br N2 O3 S'
_chemical_formula_moiety         'C28 H25 Br N2 O3 S'
_chemical_formula_structural     'C28 H25 Br N2 O3 S'
_chemical_formula_sum            'C28 H25 Br N2 O3 S'
_chemical_formula_weight         549.47
_chemical_name_common            MPL-X-119#1
_chemical_name_systematic
; 
(4<i>R</i>,12b<i>S</i>)-4-(4-Bromophenyl)-12-tosyl-1,3,4,6,7,12b-
hexahydro-indolo[2,3-<i>a</i>]quinolizin-2(12<i>H</i>)-one
;
_space_group_IT_number           19
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_computing_data_reduction
;
SAINT V7.34A (Bruker AXS, 2006b), SADABS (Bruker AXS, 2004)
;
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_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1534 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
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_diffrn_standards_decay_%        0
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_exptl_crystal_colour            Colorless
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_exptl_crystal_description       Plate
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         7164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0521
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_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^)+(0.0284P)^2^+0.5871P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                5787
_reflns_number_total             7164
_reflns_threshold_expression     I>2\s(I)
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