A new chiral lithium amide based on (S)-2-[1-(3,3-dimethyl)pyrrolidinylmethyl]pyrrolidine—synthesis, NMR studies and use in the enantioselective deprotonation of cyclohexene oxide

Khan, Agha Zul-Qarnain; Groot, Rimke W de; Arvidsson, Per I.; Davidsson, Öjvind

doi:10.1016/s0957-4166(98)00085-8

Cited by 18 publications

References 23 publications

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Die Chemie vicinaler Diamine

1998

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Vor allem bei enantioselektiven Synthesen werden vicinale Diamine (1,2‐Diamine) 1 und Verbindungen, die auf einfachem Weg aus diesen erhalten werden können – wie 1,2‐Bisimine, 1,2‐Diamide oder Imidazolidin‐2‐one –, in großem Umfang von Organikern verwendet. Mehrere Verfahren wurden entwickelt, um diese Verbindungen selektiv herzustellen. Auch viele Naturprodukte und Medikamente enthalten die 1,2‐Diaminostruktur.

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Die Chemie vicinaler Diamine

1998

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Reactivity of oxiranes with organolithium reagents

Chemla

Vrancken

2004

The Chemistry of Organolithium Compounds

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Asymmetric Transformations by Deprotonation Using Chiral Lithium Amides

Simpkins

Weller

2012

Organic Reactions

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Lithium dialkylamides, especially lithium diisopropylamide (LDA), are valuable bases in organic synthesis but it is only since 1980 that their chiral counterparts have found application in reactions that can be broadly defined as asymmetric deprotonations. This chapter provides a comprehensive overview of all selective deprotonation processes mediated by chiral lithium amides, including desymmetrizations, kinetic resolutions, and other applications such as regioselective enolizations of chiral substrates. The chapter covers the entire substrate scope of chiral lithium amide deprotonation reactions, which includes rearrangement of epoxides to allylic alcohols, enolizations of carbonyl compounds (principally, but not exclusively, cyclic ketones), and metalations of organometallics (especially tricarbonyl(η 6 ‐arene)chromium(0) complexes) and miscellaneous phosphorous‐ or sulfur‐containing compounds. It is possible to perform some benchmark reactions under “catalytic conditions,” i.e., using substoichiometic quantities of chiral lithium amide, particularly epoxide rearrangements. The capability of deprotonations, mediated by chiral lithium amides, to deliver non‐racemic intermediates with acceptable selectivity for target synthesis is amply illustrated by the examples included in the review. In particular, the desymmetrization of conformationally biased prochiral cyclic ketones has become a well‐established strategy for organic synthesis, and has seen significant application in target‐oriented synthesis.

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A new chiral lithium amide based on (S)-2-[1-(3,3-dimethyl)pyrrolidinylmethyl]pyrrolidine—synthesis, NMR studies and use in the enantioselective deprotonation of cyclohexene oxide

Cited by 18 publications

References 23 publications

Die Chemie vicinaler Diamine

Die Chemie vicinaler Diamine

Reactivity of oxiranes with organolithium reagents

Asymmetric Transformations by Deprotonation Using Chiral Lithium Amides

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