Double Reduction of Cyclic Aromatic Sulfonamides:  A Novel Method for the Synthesis of 2- and 3-Aryl-Substituted Cyclic Amines

Abstract

The facile double reduction of bicyclic aromatic sulfonamides was used to synthesize a variety of 2- and 3-aryl-substituted pyrrolidines and 2-phenylpiperidine. The method features a combined nitrogen protection and a traceless tether for the transposition of the aromatic moiety from nitrogen to carbon.

Chemistry of Bridged Lactams and Related Heterocycles

“…293,294 Recently, a similar Heck reaction protocol was utilized by Paquette to construct bridged sultams containing [4.3.1] and [4.2.1] ring systems (Scheme 102), 295,431 while Evans reported the synthesis of bridged sultams containing [3.2.1] scaffolds via a tandem Heck reaction/hydrogenation process (Scheme 103). 432–436 …”

“…432–434 The reaction can be conducted by treatment of the bridged sultams with lithium or sodium metal in ammonia. 432 The use of lithium/ethylenediamine (Benkeser reduction) afforded partially dearomatized products, while sodium naphthalenide led to extensive decomposition. 432 …”

Transition metals in organic synthesis: Highlights for the year 2005

“…(31)) [436] and of alkenes with O-pentafluorobenzoylamidoximes [437] were reported. Intramolecular Heck reactions [394,[438][439][440][441][442] were used as the key step toward an array of synthetic targets for example, stephacidin A [443], 1-epi aglycon of cripowellins A and B [444], hamigeran B [202], mensacarcin [445], (−)-galanthamine and (−)-morphine [446], gelsemine [447], 5-substituted azepino [3,4-b]indoles [448], komaroviquinone and faveline methyl ether [449], pseudopteroxazole [450], diazonamide A [75], 4,7-azaindoles [451], substituted tryptophans (Eq. (32)) [452], 3,5,7-substituted indoles [453], morphine fragments [454], (+)-wortmannin [255], umbrosone [85] and the tricyclic core of cyathin diterpenoids [455].…”

“…A large variety of ring systems were prepared via alkene-alkene RCM using ruthenium catalysts [441] including, furans and pyrroles [1062], macrocycles [1063][1064][1065][1066][1067][1068][1069][1070][1071], five-to nine-membered unsaturated cyclic amines [498,519,898,[1072][1073][1074][1075][1076][1077], cyclooctenes [1078], chiral azepin-3-ols and azocin-3-ols [1079], oxepinand oxocin-annulated 2-quinolones [1080], benzazepines [1081,1082], 1-azaspiro [5.5]undacanes [1083], N-sulfonyl-2-quinolinones [1084], bis(silyl)- [3]-ferrocenophanes [1085], ferroceno-quinolines and -isoquinolines [1086], polycyclic hydrocarbons [1087], cyclic ␣-arylthiophosphonate esters [1088], carbohydrate-based macrolides [1089], fused carbazoles [157], 4-methyl-5-alkyl-2(5H)-furanones [1090], bibicyclo [8.8.8]hexacosanes [1091], bicyclic imidazoles [1092], bicyclic phosphates [1093], bicyclic lactams [1094], hexofuranose-like imino sugars [1095], C8-glycomimeti...…”

Catalytic Asymmetric Transannulation of NH‐1,2,3‐Triazoles with Olefins

“…To the best of our knowledge, this is the first example of a chiral Brønsted acid-catalyzed rearrangement of cyclopropyl imines into enantioenriched 2,3-dihydropyrroles. Manipulation of the products should enable asymmetric synthesis of cyclic amines, amino acid analogs, [17] and complex polycyclic architectures [18] found in natural products and pharmaceutically useful compounds. These studies, along with computational investigations, are currently underway.…”