Chiral 1,2-Amino Alcohols and 1,2-Diamines Derived from Cyclohexene Oxide: Recent Applications in Asymmetric Synthesis

Abstract

This Account describes convenient procedures for the preparation of several enantiopure β-amino alcohols and β-diamines, which have proved to be efficient ligands in relevant ste­reoselective reactions such as alkylation of enolates and hydrogenation of carbonyl compounds. Furthermore, the title compounds are useful precursors of various chiral oxazolidinones, oxazinones, phosphonamides, etc., which allow the enantioselective formation of a wide variety of chiral derivatives, including alcohols, aldol condensation products, aminophosphonic acids, sulfoxides, and others, as well as the development of derivatizing reagents for the determination of enantiomeric purity in chiral alcohols and chiral amines.

• 1 Introduction

• 2 Chiral Cyclic 1,2-Amino Alcohols Derived from Cyclohexene Oxide

• 2.1 Synthesis of Enantiopure Cyclic 1,2-Amino Alcohols Derived from Cyclohexene Oxide

• 2.2 Enantioselective Addition of Diethylzinc to Aldehydes in the Presence of Chiral Cyclic 1,2-Amino Alcohols as Ligands

• 2.3 Synthesis of Chiral 1,4-Oxazin-2-ones and their Diastereoselective α-Alkylation

• 3 Synthesis of cis- and trans-Hexahydrobenzoxazolidin-2-ones and their Application as Chiral Auxiliaries in Asymmetric Synthesis

• 3.1 Diastereoselective α-Alkylation

• 3.2 Diastereoselective Aldol Reaction

• 3.3 Regio- and Diastereoselective C-Acylation

• 3.4 Stereospecific Chiral Sulfinyl Transfer Agents

• 3.5 Stereoselective Michael Addition

• 3.6 Diastereoselective Azidation

• 4 Chiral Cyclic 1,2-Diamines Derived from Cyclohexene Oxide

• 4.1 Synthesis of Enantiopure Cyclic 1,2-Diamines

• 4.2 Application of Phosphorylated Derivatives of Enantiopure 1,2-Diamines as Chiral Derivatizing Agents

• 4.3 Enantioselective Reduction of Acetophenone in the Presence of Enantiopure 1,2-Diamines

• 4.4 Synthesis of Sulfonamide Ligands and their Application in the Enantioselective Alkylation, Vinylation and Allylation of Ketones

• 4.5 Diastereoselective Addition of Phosphorylated Derivatives to Aldehydes

Key words

enantiopure β-amino alcohols and β-diamines - chiral ligands - alkylation of enolates - chiral oxazolidinones - determination of enantiomeric purity

References and Notes

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Reyes-Rangel, G.; Marañón, V.; Avila-Ortiz, G.; Anaya de Parrodi, C.; Quintero, L.; Juaristi, E. Tetrahedron, 2006, 62, 8404