Synthesis of azepines by a gold-catalyzed intermolecular [4 + 3]-annulation.
نویسندگان
چکیده
A convenient gold(III)-catalyzed synthesis of azepines from the intermolecular annulation of propargyl esters and alpha,beta-unsaturated imines is reported (19 examples, 55-95% yield). This formal [4 + 3]-cycloaddition reaction is proposed to proceed via a stepwise process involving intramolecular trapping of an allyl-gold intermediate.
منابع مشابه
Anionic [4+3] heteroannulation of 2-azidoacrylates: a modular synthesis of 2-benzazepin-1-ones.
2-Azidoacrylates undergo [4+3] annulation with phthalides under anionic conditions at low temperatures to furnish 5-hydroxy-2-benzazepinones, the formation of which represents a new concept for the construction of azepines as well as a new reactivity of 2-azidoacrylates.
متن کاملSynthesis of benzonorcaradienes by gold(I)-catalyzed [4+3] annulation.
A formal [4 + 3]-annulation of vinyl arenes and diynyl propargyl esters is described. A mechanism involving cationic phosphinegold(I)-catalyzed tandem cyclopropanation/hydroarylation to produce the benzonorcaradiene products is proposed. In accord with this mechanism, the alkynyl cyclopropane can also be prepared with excellent regio- and diastereocontrol.
متن کاملGold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.
A surprisingly efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation is developed. This reaction involves a key gold catalysis and shows generally high regioselectivities and good to excellent diastereoselectivities.
متن کاملPd-catalyzed dehydrogenative annulation approach for the efficient synthesis of phenanthridinones
A novel Pd-catalyzed intermolecular dehydrogenative annulation of aryl iodides and aryl carbamic chlorides for the efficient synthesis of phenanthridinone derivatives was developed. Simple aryl iodides and carbamic chlorides readily made from various anilines, a broad substrate scope with hetero/polycycles, as well as high-value products, make this direct dehydrogenative annulation approach ver...
متن کاملPhosphine-catalyzed domino reaction: an efficient method for the synthesis of highly functionalized spirooxazolines.
A novel phosphine-catalyzed intermolecular [3 + 2] cycloaddition of ynones and N-substituted isatins was developed. In this reaction, substituted ynones, serving as a C(3) synthon, were successfully applied in intermolecular annulation reactions. A number of functionalized spirooxazolines were obtained in high yields and stereoselectivity.
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:
- Journal of the American Chemical Society
دوره 130 29 شماره
صفحات -
تاریخ انتشار 2008