Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives.
نویسندگان
چکیده
This article describes the aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones and subsequent transformations that highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine nucleophile in this transformation.
منابع مشابه
ZnCl2-catalyzed chemoselective cascade reactions of enaminones with 2-furylcarbinols: a versatile process for the synthesis of cyclopenta[b]pyrrole derivatives.
A highly efficient ZnCl2-catalyzed cascade reaction of enaminones with 2-furylcarbinols under mild reaction conditions has been developed. This methodology offers a chemo- and diastereo-selective access to functionalized cyclopenta[b]pyrrole derivatives in good to excellent yields.
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The first catalytic asymmetric Piancatelli reaction is reported. Catalyzed by a chiral Brønsted acid, the rearrangement of a wide range of furylcarbinols with a series of aniline derivatives provides valuable aminocyclopentenones in high yields as well as excellent enantioselectivities and diastereoselectivities. The high value of the aza-Piancatelli rearrangement was demonstrated by the synthe...
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number of elegant approaches to construct azaspirocycles have been developed. The methods differ in the strategy used to address the two main synthetic challenges: construction of the tertiary carbon center bearing the nitrogen atom, and the formation of the spirocyclic ring system. Generally, the synthetic routes rely on a two-step process where the tertiary carbon center and the spirocycle ar...
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BACKGROUND Indolizidine alkaloids widely occur in nature and display interesting biological activity. This is the reason for which their total synthesis as well as the synthesis of non-natural analogues still attracts the attention of many research groups. To establish new straightforward accesses to these molecules is therefore highly desirable. RESULTS The ring closing metathesis (RCM) of e...
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...
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عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 13 31 شماره
صفحات -
تاریخ انتشار 2015