Double Dehydro‐Diels–Alder Reactions of 1,5‐Dien‐3‐ynes | Zendy

Fallon Thomas | Zendy; Robinson Diane E. J. E. | Zendy; Willis Anthony C. | Zendy; PaddonRow Michael N. | Zendy; Sherburn Michael S. | Zendy

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Double Dehydro‐Diels–Alder Reactions of 1,5‐Dien‐3‐ynes

Author(s) -

Fallon Thomas,

Robinson Diane E. J. E.,

Willis Anthony C.,

PaddonRow Michael N.,

Sherburn Michael S.

Publication year - 2010

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.200902190

Subject(s) - allene , cycloaddition , double bond , stereoselectivity , chemistry , diels–alder reaction , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis

Allene towards efficiency : Two new rings, six stereocentres and four CC bonds are generated in synthetically useful yields by double dehydro‐Diels–Alder reactions of readily available 1,5‐dien‐3‐ynes and alkenic dienophiles. Computational studies support a mechanism for this often highly stereoselective process involving two concerted cycloaddition events and a 1,2‐cyclohexadiene intermediate (see scheme).

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