Sultame

1λ ⁶ , 2-thiazinane-1,1-dione or 1,2-thiazinane-1,1-dioxide or butane-1,4-sultam

As sultams refers to a class of chemical compounds , referred to as cyclic amides of sulfonic acid can be considered. Their analogues in carbon chemistry are the lactams . The name Sultam comes from Sul fonsäure-Lac tam . Sultams are heterocyclic compounds having a hexavalent sulfur - and an adjacent nitrogen - atom within the ring, thus a endocyclic -NH-SO ₂ group.

β-sultam of penicillanic acid
R = Na or H

The best-known representative of this class of compounds is the sweetener saccharin .

β-sultams are accessible via the sulfa-Staudinger synthesis . The sulfur analogues of β-lactams are of medicinal and chemical interest insofar as they are similar to penicillin .

Oppolzer-Sultam

In addition, sultams are used as chiral auxiliaries in asymmetric synthesis. The best known connection is the Oppolzer-Sultam . It can be used in asymmetric dihydroxylations , Diels-Alder reactions , alkylations or asymmetric hydrogenations .

Finally, β-sultams were used as a catalyst in enantioselective synthesis.

The sultams are in equilibrium with their tautomeric form, which are known as sultams . This isomerism is similar to lactam- lactim tautomerism.

Propane-4-sultim

Web links

• Synthesis sultame

Individual evidence

1. ↑ HH Otto, P. Schwenkkraus. In: Tetrahedron Lett. 23 (1982), p. 5389.
2. ↑ P. Schwenkkraus, HH Otto. In: Arch. Pharm. , 1993, p. 437.
3. ↑ M. Müller, HH Otto. In: Liebigs Ann. Chem. 1991, p. 171.
4. ↑ AWM Lee, WH Chan, WH Yuen, PF Xia, WY Wong. In: Tetrahedron: Asymmetry , 10 (1999), p. 1421.
5. ^ WH Chan, AWM Lee, LS Kiang, TCW Mak. In: Tetrahedron: Asymmetry , 8, (1007), p. 2501.
6. ↑ J. Lin, WH Chan, AWM Lee, WY Wong. In: Tetrahedron , 55 (1999), p. 13983.
7. ^ W. Oppolzer, RJ Mills, M. Reglier. In: Tetrahedron Lett. , 27 (1986), p. 183.
8. ^ W. Trentmann, T. Mehler, J. Martens . In: Tetrahedron: Asymmetry , 8 (1997), p. 2033.