Synthesis and Properties of β-sultams

Twisting and Turning the Sulfonamide Bond: A Synthetic, Quantum Chemical, and Crystallographic Study

“…The synthetic part of this work was aimed mainly at the preparation of bicyclic sultams shown in Figure (since the synthesis is trivial for compounds 9 – 14 , whereas sultams 15 and 16 can be obtained by a reported method). It should be noted that none of the Paquette’s sultams were prepared previously via formation of the sulfonamide bond, a retrosynthetic disconnection that might be anticipated as the most obvious.…”

Versatile Synthesis of Free and N‐Benzyloxycarbonyl‐Protected 2,2‐Disubstituted Taurines

“…2‐Amino‐2‐methylpropanesulfonic acid, the simplest 2,2‐disubstituted taurine, has been synthesized from 2‐methylalanine,12 acetone cyanohydrin,12 and 2,2‐dimethyl‐β‐sultam 13. We also prepared 2,2‐dialkyl‐substituted taurines efficiently from 2,2‐dialkyl‐substituted aziridines.…”

“…Recently, α,α‐disubstituted amino acids have been widely used as building blocks to prepare peptidomimetics for peptide‐like drug discovery with better biological stability 7–10. As sulfur analogues of naturally occurring amino acids, some gem ‐disubstituted aminoalkanesulfonic acids,11–13 a series of 1,1‐disubstituted taurines,11 and a few 2,2‐disubstituted taurines12,13 and vic ‐disubstituted taurines14–17 have been synthesized to date. For the investigation of biological activities and structure–activity relationships, the discovery of peptidomimetic drug, and the synthesis of sulfonopeptides, we wish to develop efficient methods to prepare structurally diverse substituted taurines.…”

Novel Reagent Space: Identifying Unorderable but Readily Synthesizable Building Blocks

“…An attempt to prepare alcohol 21 via alkylation of sultam 43 with bromide 44 was not successful; the sultam was consumed, and none of the desired alcohol was isolated, potentially due to the tendency of βsultams to open under basic conditions. 38 Regarding alcohol 18, our initial attempt to effect the transformation proposed by the ASKCOS tool (retrosynthesis shown in Scheme 3) was unsuccessful; upon treatment with NaH in THF, 37 and 38 did not provide any of the desired product (Scheme 4). However, a modified route using the same available reagent was successful at attaching moiety 18 to the LO molecule to provide 47.…”

“…Likewise, the alkylation to prepare 20 proceeded smoothly, albeit through the TBDPS ether of 41 . An attempt to prepare alcohol 21 via alkylation of sultam 43 with bromide 44 was not successful; the sultam was consumed, and none of the desired alcohol was isolated, potentially due to the tendency of β-sultams to open under basic conditions …”