Topic
Carroll rearrangement
About: Carroll rearrangement is a research topic. Over the lifetime, 1483 publications have been published within this topic receiving 23513 citations.
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TL;DR: Adding an aryne to a tertiary allylamine affords o-allylaniline products of an aza-Claisen rearrangement that was applied to the synthesis of medium-ring benzannulated amines.
Abstract: Adding an aryne to a tertiary allylamine affords o-allylaniline products of an aza-Claisen rearrangement. The aryne simultaneously provides the pi component for the rearrangement and the quaternization event that lowers the activation energy for the sigmatropic shift. The reaction was applied to the synthesis of medium-ring benzannulated amines (see scheme).
100 citations
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TL;DR: Allylic esters of heteroaromatic alkanes undergo facile palladium-catalyzed decarboxylative coupling, and the resulting C−C bond is formed with high diastereoselectivity and high regioselectivities for coupling at the more substituted allyl terminus.
Abstract: Allylic esters of heteroaromatic alkanes undergo facile palladium-catalyzed decarboxylative coupling. The resulting C−C bond is formed with high diastereoselectivity and high regioselectivity for coupling at the more substituted allyl terminus. It is proposed that this unusual combination of selectivities results from a tandem allylation/aza-Cope rearrangement sequence. After allylation, decarboxylative dearomatization produces an intermediate for the aza-Cope rearrangement. The subsequent aza-Cope rearrangement occurs under mild conditions because it is driven by rearomatization.
98 citations
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97 citations
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96 citations