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Tandem RCM-Claisen rearrangement-[2+2] cycloaddition of O,O'-(but-2-en-1,4-diyl)-bridged binaphthols.

ABSTRACT: Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided.

SUBMITTER: Abraham M

PROVIDER: S-EPMC6268543 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Tandem RCM-Claisen rearrangement-[2+2] cycloaddition of O,O'-(but-2-en-1,4-diyl)-bridged binaphthols.

Abraham Michael M Reischl Wolfgang W Kirchner Karl A KA Roller Alexander A Veiros Luis F LF Widhalm Michael M

Molecules (Basel, Switzerland) 20121207 12

Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided. ...[more]

PMID: 23222901

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