Aza-Piancatelli rearrangement initiated by ring opening of donor-acceptor cyclopropanes.
نویسندگان
چکیده
The development of a new platform to initiate the cascade rearrangement of furans for the formation of functionalized cyclopentenone building blocks is reported. This methodology allows the creation of congested vicinal stereogenic centers with high diastereoselectivity through a 4π-electrocyclization process.
منابع مشابه
Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo- philes
Abstract Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitri...
متن کاملCyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes.
Cyclization and annulation reactions initiated by ring-opening of small rings, especially cyclopropanes and cyclobutanes are now well-established in synthetic chemistry. Nevertheless, the potential of aminocyclopropanes and cyclobutanes, an important subclass for the synthesis of nitrogen-rich building blocks, has remained unexploited for a long time, despite important pioneering results. In th...
متن کاملRing-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
Donor-acceptor cyclopropanes with two geminal carboxylic esters are reacted with chalcogenyl chlorides and bromides to afford ring-opened products bearing the halogen atoms in the 1-position, adjacent to the donor, and the chalcogenyl residue in the 3-position next to the two acceptor groups. A variety of different donors (e.g., aryl, N, and O) are used. The stereospecificity of the reaction is...
متن کاملOne-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes.
A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor-acceptor cyclopropanes and subsequent in situ reduction of enamine (imine) intermediates.
متن کاملVersatile method for the synthesis of 4-aminocyclopentenones: dysprosium(III) triflate catalyzed aza-piancatelli rearrangement.
Well-represented in natural products and biologically active molecules, the cyclopentenone scaffold has long been an inspiration for the development of new methodologies. In 1976, Piancatelli and co-workers reported a new method for the synthesis of 4-hydroxycyclopentenone derivatives by an acid-catalyzed rearrangement of suitable 2-furylcarbinols (Scheme 1). The overall transformation is belie...
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 letters
دوره 15 13 شماره
صفحات -
تاریخ انتشار 2013