| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346409 | Tetrahedron: Asymmetry | 2011 | 8 Pages |
A series of novel heteroarylidene malonate derived bis(thiazoline) ligands 1 and 2 were synthesized and applied to a Friedel–Crafts reaction between indole and alkylidene malonate. The Cu(OTf)2 complex of ligand 2b bearing a benzyl group afforded moderate to excellent enantioselectivity for the adducts (up to >99% ee).
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(S,S)-N,N-Bis(2-TBDMSO-1-iso-propyl)-2-(2-thienylmethylidene)malonamideC30H56N2O4SSi2Ee = 100%[α]D25=-49.2 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMSO-1-benzyl)-2-(2-thienylmethylidene) malonamideC38H56N2O4SSi2Ee = 100%[α]D25=-85.6 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMSO-1-phenyl)-2-(2-thienylmethylidene) malonamideC36H52N2O4SSi2Ee = 100%[α]D25=-35.0 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMS-1-iso-propyl)-2-(2-furylmethylidene) malonamideC30H56N2O5Si2Ee = 100%[α]D25=-121.2 (c 0.30, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMS-1-benzyl)furylmethylidene) malonamideC36H52N2O5Si2Ee = 100%[α]D25=-87.2 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMS-1-phenyl)-2-(2-furylmethylidene) malonamideC36H52N2O5Si2Ee = 100%[α]D25=-88.0 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMSO-1-iso-propyl)-2-(2-thienylmethylidene)thio-malonamideC30H56N2O2S3Si2Ee = 100%[α]D25=-155.5 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMSO-1-benzyl)-2-(2-thienylmethylidene) thio-malonamideC38H56N2O2S3Si2Ee = 100%[α]D25=-112.8 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMSO-1-phenyl)-2-(2-thienylmethylidene) thio-malonamideC36H52N2O2S3Si2Ee = 100%[α]D25=-62.4 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMSO-1-iso-propyl)-2-(2-furylmethylidene) thio-malonamideC30H56N2O3S2Si2Ee = 100%[α]D25=-140.5 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMSO-1-benzyl)-2-(2-furylmethylidene) thio-malonamideC38H56N2O3S2Si2Ee = 100%[α]D25=-111.2 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
(S,S)-N,N-Bis(2-TBDMSO-1-phenyl)-2-(2-furylmethylidene) thio-malonamideC36H52N2 O3S2Si2Ee = 100%[α]D25=-29.6 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S,S)
Bis[(S)-4-(iso-propyl)thiazoline-2-yl]-2-thienyletheneC18H24N2S3Ee = 100%[α]D25=-89.6 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S)
Bis[(S)-4-benzylthiazoline-2-yl]-2-thienyletheneC26H24N2S3Ee = 100%[α]D25=+25.6 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S)
Bis[(S)-4-phenylthiazoline-2-yl]-2-thienyletheneC24H20N2S3Ee = 100%[α]D25=+42.0 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S)
Bis[(S)-4-(iso-propyl)thiazoline-2-yl]-2-furyletheneC18H24N2OS2Ee = 100%[α]D25=-44.4 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S)
Bis[(S)-4-benzylthiazoline-2-yl]-2-furyletheneC26H24N2OS2Ee = 100%[α]D25=-17.6 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S)
Bis[(S)-4-phenylthiazoline-2-yl]-2-furyletheneC24H20N2OS2Ee = 100%[α]D25=+105.4 (c 0.25, CH2Cl2)Source of chirality: l-amino alcoholAbsolute configuration: (S)
