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Progress in the Asymmetric Synthesis of 1,2-Diamines from Azomethine Compounds

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Chiral Diazaligands for Asymmetric Synthesis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 15))

Abstract

Recent advances in the preparation of optically pure 1,2-diamines by stereoselective addition reactions to azomethine compounds (imines, iminium ions, oximes, hydrazones, nitrones) are discussed. The methods scrutinized involve either the addition of carbon nucleophiles (organometallic reagents, carbanions, enolates, silyl enol ethers, carbon radicals and radical anions) to aldehyde derivatives, e.g., aldimines, and the complementary addition of hydrogen and hydride reagents to ketone derivatives, e.g., ketimines. Focus is given to the scope, advantages and limitations of the diverse methodologies and some possible developments are envisaged.

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Abbreviations

Boc:

tert-Butyloxycarbonyl

Cbz:

Carboxybenzyl

CSA:

(+)-Camphorsulfonic acid

de:

Diastereomeric excess

DMF:

N,N-Dimethylformamide

dr:

Diastereomeric ratio

ee:

Enantiomeric excess

HMPTA:

Hexamethylphosphoric triamide

PMP:

para-Methoxyphenyl

THF:

Tetrahydrofuran

TMEDA:

Tetramethylethylenediamine

TMS:

Trimethylsilyl

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Authors and Affiliations

  1. Dipartimento di Chimica “G. Ciamician”, Università di Bologna, via Selmi 2, 40126, Bologna, Italy

    Diego Savoia

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  1. Diego Savoia
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Marc Lemaire Pierre Mangeney

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Savoia, D. Progress in the Asymmetric Synthesis of 1,2-Diamines from Azomethine Compounds. In: Lemaire, M., Mangeney, P. (eds) Chiral Diazaligands for Asymmetric Synthesis. Topics in Organometallic Chemistry, vol 15. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136347

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