Gold-catalysed synthesis of amino acid-derived 2,5-disubstituted oxazoles.
نویسندگان
چکیده
Amino acid-derived propargylic amides are cyclised in a one-pot, Au(III)-catalysed operation to yield 5-bromomethyl oxazoles. These compounds are further elaborated to bis-heterocycles, dipeptide mimics and more.
منابع مشابه
Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline.
An efficient two-step palladium catalysed synthesis of 2,5-disubstituted oxazoles is reported.
متن کاملRoom temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization.
A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to affor...
متن کاملCatalytic hetero-ene reactions of 5-methyleneoxazolines: highly enantioselective synthesis of 2,5-disubstituted oxazole derivatives.
An efficient catalytic asymmetric hetero-ene reaction of 5-methyleneoxazolines with 1,2-dicarbonyl compounds (including α-ketoesters and glyoxal derivatives) was realized using Ni(II)-N,N'-dioxide complexes as the catalysts. It provides a rapid, high yielding (up to 99%) route for the preparation of 2,5-disubstituted oxazole derivatives in a highly enantioenriched form (up to >99% ee) under mil...
متن کاملUnconventional oxazole formation from isocyanides.
The coupling of an acyl chloride with an isocyanide affords 2,5-disubstituted oxazoles under mild basic conditions instead of 4,5-disubstituted derivatives when using Schöllkopf conditions (butyllithium); this reaction constitutes a remarkable example of a base-induced chemoselective process in isocyanide chemistry.
متن کاملEfficient, stereoselective synthesis of trans-2,5-disubstituted morpholines.
[reaction: see text] Enantio- and diastereoselective syntheses of trans-2,5-disubstituted morpholine derivatives are described. The routes are initiated by the reaction of enantiopure epoxides (2) with amino alcohols (3) and address the problem of regioselective hydroxyl activation-ring closure of the resulting amino diol adducts for (amino alcohol-derived) alkyl substituents of different steri...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 9 11 شماره
صفحات -
تاریخ انتشار 2011