| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348723 | Tetrahedron: Asymmetry | 2010 | 6 Pages |
The chiral cyclosulfamide (S)-2-benzyl-4-isopropyl-1,2,5-thiadiazolidine 1,1-dioxide was designed as a chimera of Evans and Oppolzer chiral auxiliaries. The N-propionyl derivative appeared to be very powerful for the stereocontrolled synthesis of chiral building blocks through asymmetric aldolization and alkylation reactions.
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N′-[(1S) 2-Hydroxy-1-isopropylethyl]-N,N-dimethylsulfonamideC7H18N2O3S[α]D20=-35 (c 1.2, CHCl3)Source of chirality: l-valinolAbsolute configuration: (1S)
(2S)-2-Isopropyl-N,N-dimethylaziridine-1-sulfonamideC7H16N2O2S[α]D20=+52.7 (c 1.1, CHCl3)Source of chirality: N′-[(1S)-2-hydroxy-1-isopropylethyl]-N,N-dimethylsulfonamideAbsolute configuration: (2S)
(4S)-2-Benzyl-4-isopropyl-1,2,5-thiadiazolidine 1,1-dioxideC12H18N2O2S[α]D20=-36 (c 1.0, CHCl3)Source of chirality: (S) 2-isopropyl-N,N-dimethylaziridine-1-sulfonamideAbsolute configuration: (4S)
(3S)-5-Benzyl-3-isopropyl-2-propanoyl-1,2,5-thiadiazolidine 1,1-dioxideC15H22N2O3S[α]D20=+17 (c 1.0, CHCl3)Source of chirality: (4S) 2-benzyl-4-isopropyl-1,2,5-thiadiazolidine 1,1-dioxideAbsolute configuration: (3S)
(2′S,3′R,3S)-5-Benzyl-3-isopropyl-2-(2′,4′-dimethyl-3′-hydroxy)pentanoyl-1,2,5-thiadiazolidine 1,1-dioxideC19H30N2O4S[α]D20=+25 (c 1, CHCl3)Source of chirality: (3S)-5-benzyl-3-isopropyl-2-propanoyl-1,2,5-thiadiazolidine 1,1-dioxideAbsolute configuration: (2′S,3′R,3S)
(2′S,3′S,3S)-5-Benzyl-3-isopropyl-2-(3′-hydroxy-2′-methyl-3′-phenyl)propanoyl-1,2,5-thiadiazolidine 1,1-dioxideC22H28N2O4S[α]D20=+20 (c 1.0, CHCl3)Source of chirality: (3S)-5-benzyl-3-isopropyl-2-propanoyl-1,2,5-thiadiazolidine 1,1-dioxideAbsolute configuration: (2′S,3′S,3S)
(2′S,3′R,3S)-5-Benzyl-3-isopropyl-2-(-3′-hydroxy-2′-methyl)hexanoyl-1,2,5-thiadiazolidine 1,1-dioxideC19H30N2O4S[α]D20=+30 (c 1.0, CHCl3)Source of chirality: (3S) 5-benzyl-3-isopropyl-2-propanoyl-1,2,5-thiadiazolidine-1,1-dioxideAbsolute configuration: (2′S,3′R,3S)
(2′S,3′R,3S)-5-Benzyl-3-isopropyl-2-(3′-cyclohexyl-3′-hydroxy-2′-methyl)propanoyl-1,2,5-thiadiazolidine 1,1-dioxideC22H34N2O4S[α]D20=+31 (c 1.0, CHCl3)Source of chirality: (3S)-5-benzyl-3-isopropyl-2-propanoyl-1,2,5-thiadiazolidine 1,1-dioxideAbsolute configuration: (2′S,3′R,3S)
(2′S,3S)-5-Benzyl-3-isopropyl-2-(2′-methyl-3′-phenyl)-propanoyl-1,2,5-thiadiazolidine 1,1-dioxideC22H28N2O3S[α]D20=-90 (c 0.3, CHCl3)Source of chirality: (3S)-5-benzyl-3-isopropyl-2-propanoyl-1,2,5-thiadiazolidine 1,1-dioxideAbsolute configuration: (2′S,3S)
(2′S,3S)-5-Benzyl-3-isopropyl-2-(-2′-methyl)pent-4′-enoyl-1,2,5-thiadiazolidine 1,1-dioxideC18H26N2O3S[α]D20=-4 (c 0.5, CHCl3)Source of chirality: (3S) 5-benzyl-3-isopropyl-2-propanoyl-1,2,5-thiadiazolidine 1,1-dioxideAbsolute configuration: (2′S,3S)
