- Direct Synthesis of Allyl Amines with 2-Nitrosulfonamide Derivatives via the Tsuji-Trost Reaction
-
The Tsuji-Trost Reaction is a palladium-catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen-based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2-nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2-nitrosulfonyl groups are well-known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2-nitrosulfonamide derivatives are ideal substrates for the Tsuji-Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives.
- Bon, Corentin,Arimondo, Paola B.,Halby, Ludovic
-
-
Read Online
- A Synthetic Bioinspired Carbohydrate Polymer with Mucoadhesive Properties
-
Mucoadhesive polymers are of significant interest to the pharmaceutical, medical device, and cosmetic industries. Polysaccharides possessing charged functional groups, such as chitosan, are known for mucoadhesive properties but suffer from poor chemical d
- Balijepalli, Anant S.,Sabatelle, Robert C.,Chen, Mingfu,Suki, Bela,Grinstaff, Mark W.
-
supporting information
p. 704 - 710
(2019/12/11)
-
- Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex
-
A benchtop-stable reagent for the catalytic Nicholas reaction was developed. By combining a propargyl dicobalt hexacarbonyl cluster with an ortho-alkynylbenzoate unit and a fluorous tag, introduction of a propargyl hexacarbonyl complex on various aromatic compounds having acid- or base-sensitive functional groups becomes possible by using a gold(i) catalyst. In addition, the presence of a fluorous tag facilitates convenient separation of the target products from byproducts.
- Okamura, Toshitaka,Fujiki, Shogo,Iwabuchi, Yoshiharu,Kanoh, Naoki
-
supporting information
p. 8522 - 8526
(2019/10/02)
-
- Enantioselective IrI-catalyzed carbocyclization of 1,6-enynes by the chiral counterion strategy
-
Enantioenriched bicyclo[4.1.0]hept-2-enes were synthesized by Ir I-catalyzed carbocyclization of 1,6-enynes. No chiral ligands were used, CO and PPh3 were the only ligands bound to iridium. Instead, the stereochemical information was
- Barbazanges, Marion,Auge, Mylene,Moussa, Jamal,Amouri, Hani,Aubert, Corinne,Desmarets, Christophe,Fensterbank, Louis,Gandon, Vincent,Malacria, Max,Ollivier, Cyril
-
experimental part
p. 13789 - 13794
(2012/01/06)
-
- HEAVY-NITROGENIZED NITROBENZENESULFONAMIDE, ITS DERIVATIVE AND PRODUCTION METHOD THEREOF
-
PROBLEM TO BE SOLVED: To provide a heavy-nitrogenized nitrobenzenesulfonamide derivative and an efficient production method thereof. SOLUTION: The heavy-nitrogenized nitrobenzenesulfonamide compound is represented by general formula [2]. An amino group of
- -
-
Page/Page column 25-26
(2008/06/13)
-
- Ruthenium catalyzed ring rearrangement: A rapid entry to substituted aza- and oxacycles
-
A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloh
- Ovaa, Huib,Stapper, Christian,Van Der Marel, Gijs A,Overkleeft, Hermen S,Van Boom, Jacques H,Blechert, Siegfried
-
p. 7503 - 7518
(2007/10/03)
-
- New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides
-
A new route for the asymmetric synthesis of 4-aminocyclopent-2-en-1-ols (90% ee) for carbocyclic nucleoside analogue synthesis is described. The approach involves the stereoselective preparation of cis 4-amino-substituted cyclopentene oxides and subsequent chiral base-mediated rearrangement to the corresponding allylic alcohols. Full details on the synthesis and stereoselectivity of epoxidation of 4-amino-substituted cyclopentenes are presented. (C) 2000 Elsevier Science Ltd.
- Barrett, Stephen,O'Brien, Peter,Steffens, H.Christian,Towers, Timothy D,Voith, Matthias
-
p. 9633 - 9640
(2007/10/03)
-
- N-carboalkoxy-2-nitrobenzenesulfonamides: A practical preparation of N- Boc-, N-Alloc-, and N-Cbz-protected primary amines
-
N-Carboalkoxy-2-nitrobenzenesulfonamides, readily prepared by acylation of 2-nitrobenzenesulfonamide (o-NsNH2), can be alkylated by either conventional or Mitsunobu protocols. Since the o-nosyl group can be deprotected under mild conditions, a variety of N-carboalkoxy derivatives of primary amines may be prepared in excellent yields from the corresponding alcohols and/or halides. In addition, allyloxycarbonyl (Alloc), t- butoxycarbonyl (t-Boc), and benzyloxycarbonyl (Cbz) groups can be deprotected in the presence of the o-nosyl group, allowing the resultant N-alkylated 2- nitrobenzenesulfonamides to be used for further preparation of secondary amines.
- Fukuyama, Tohru,Cheung, Mui,Kan, Toshiyuki
-
p. 1301 - 1303
(2007/10/03)
-
- Heterocycles with a benzothiadiazepine moiety. 5. Derivatives of pyrrolo[2,1-d][1,2,5]benzothiadiazepine, a novel tricyclic ring
-
The synthesis of pyrrolo[2,1-d][1,2,5]benzothiadiazepin-7(6H)-one 5,5- dioxide has been achieved by reaction between 2-(1H-pyrrol-1- yl)benzenesulfonamide and triphosgene. N-Ethylation of the tricyclic derivative afforded 6-ethylpyrrolo[2,1-d][1,2,5]benzothiadiazepin-7(6H)-one 5,5-dioxide, also obtained by the action of trifosgene on N-ethyl 2-(1H- pyrrol-1-yl)benzenesulfonamide. Preparation of pyrrole derivatives from 2- aminobenzenesulfonamide and its N-ethyl derivative by Clauson-Kaas procedure required preliminary protection of the sulfonamide function.
- Di Santo,Costi,Artico,Massa
-
p. 375 - 378
(2007/10/03)
-