Synlett 2014; 25(6): 896-897
DOI: 10.1055/s-0033-1340855
© Georg Thieme Verlag Stuttgart · New York

Silyl Ketene Imines

Fausto Daniel dos Santos Queda
REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, ­Lisboa, Portugal   Email:
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Further Information

Publication History

Publication Date:
21 February 2014 (online)

Silyl ketene imines (SKIs) are a wide variety of nucleophiles possessing a pair of orthogonal substituents within a cumulene group and can have other functional groups, including alkenes, allenes, ketenes, and amines. SKIs can be employed in a wide range of reactions involving C–C bond formation and/or the formation of stereogenic centers.

When combined with an appropriate catalyst and ligand, C–C bond forming reactions with SKIs are highly stereo­selective. SKIs can be converted into nitriles which are precursors of many other functional groups including carboxylic acids, amines, and aldehydes.[2] One of the first synthetic applications of SKIs was described in 1987: a Diels–Alder [4+2] cycloaddition stating a versatile method to obtain anilines and cyclohexanones, leading to a range of aromatic amines in 52–89% yield.[3]

Due to their geometry and the presence of two orthogonal substituents, SKIs have proven to be excellent nucleophiles in order to obtain stereogenic centers.[4]

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