Palladium-catalyzed mono-N-allylation of unprotected amino acids with 1,1-dimethylallyl alcohol in water.
نویسندگان
چکیده
Palladium-catalyzed N-allylation of unprotected amino acids with 1,1-dimethylallyl alcohol were carried out. The reaction in the presence of Pd(OAc)(2) (5 mol%), sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol%), and AcONa (2 equiv) in water at 120 °C for 16 h in a sealed tube gave only mono-N-allylated amino acids in good yield.
منابع مشابه
[Development of unprotected syntheses in aqueous media].
Introduction of carbon side chain at C(3)-position of indole ring was accomplished by using Pd-catalyzed allylation and vinylation. The selective vinylation at C(3)-position of 4-bromoindole was applied to the synthesis of optically active 4-bromotryptophan derivatives, which was used as a starting material for the synthesis of several optically active ergot alkaloids, which were clavicipitic a...
متن کاملPalladium-catalyzed S-benzylation of unprotected mercaptobenzoic acid with benzyl alcohols in water.
Palladium-catalyzed S-benzylation of unprotected mercaptobenzoic acids with benzyl alcohols gave only S-benzylated mercaptobenzoic acids in good yields. Water may play an important role for the smooth generation of the (η(3)-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.
متن کاملDiastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols.
The palladium-catalyzed allylation of N-tert-butanesulfinyl imines with allylic alcohols in the presence of InI as reducing reagent takes place with high diastereoselectivity in reasonable yields. The reaction with crotyl alcohol is totally regioselective, leading to the anti-diastereomer as the main reaction product.
متن کاملA sequential indium-mediated aldehyde allylation/palladium-catalyzed cross-coupling reaction in the synthesis of 2-deoxy-beta-C-aryl glycosides.
Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with d-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C...
متن کاملDecarboxylative allylations of ester enolate equivalents.
A variety of ester enolate equivalents are generated in situ and undergo α-allylation in high yields via palladium-catalyzed decarboxylative allylation. The transformations are complete within very short reaction times under ambient conditions. Synthesis of α-allylated acyl derivatives provides access to other carboxylic acid and alcohol derivatives via acyl group substitution or reduction.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 9 11 شماره
صفحات -
تاریخ انتشار 2011