Chiral bifunctional guanidine-catalyzed enantioselective Aza-Henry reaction of isatin-derived ketimines.
Fang, Bing; Liu, Xiaohua; Zhao, Jiannan; Tang, Yu; Lin, Lili; Feng, Xiaoming; The Journal of organic chemistry 80 (2015) 3332–3338; doi:10.1021/acs.joc.5b00075

data_4036125
_publ_section_title
;
 Chiral bifunctional guanidine-catalyzed enantioselective Aza-Henry
 reaction of isatin-derived ketimines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3332
_journal_page_last               3338
_journal_paper_doi               10.1021/acs.joc.5b00075
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H23 N3 O5'
_chemical_formula_sum            'C21 H23 N3 O5'
_chemical_formula_weight         397.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
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Olex2 1.2
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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omega____ theta____ kappa____ phi______ frames
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  2 omega   23.00   90.00   1.0000    1.5600
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omega____ theta____ kappa____ phi______ frames
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  5 omega  -33.00  106.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
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  6 omega   23.00   90.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
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  7 omega   17.00  105.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
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  8 omega   17.00  105.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
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  9 omega   38.00   91.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
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 10 omega   39.00  109.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
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 11 omega   39.00  109.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

 12 omega   40.00   98.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 13 omega   90.00  175.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 85

 14 omega   81.00  176.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

 15 omega   91.00  176.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

 16 omega   87.00  178.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 91

 17 omega   90.00  175.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

 18 omega   39.00  109.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 19 omega   87.00  178.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 91

 20 omega   81.00  176.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 21 omega   90.00  175.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 22 omega   90.00  175.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 23 omega   38.00   91.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 24 omega   88.00  113.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 25

 25 omega   92.00  140.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 48

 26 omega   78.00  104.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 26

 27 omega   91.00  118.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 27

 28 omega  126.00  175.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 49

 29 omega   97.00  124.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 27

 30 omega  102.00  169.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 67

 31 omega   57.00  149.00   1.0000    6.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 92
;
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CrysAlisPro, Agilent Technologies,
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Empirical absorption correction using spherical harmonics,
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 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
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'w=1/[\s^2^(Fo^2^)+(0.0970P)^2^] where P=(Fo^2^+2Fc^2^)/3'
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00L(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
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;
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