A new non-natural chiral auxiliary: design, synthesis, and resolution of 1-mesitylethylamine and its application in the asymmetric aza-Diels–Alder reaction

Kohara, Takehiro; Hashimoto, Yukihiko; Shioya, Rieko; Saigo, Kazuhiko

doi:10.1016/s0957-4166(99)00579-0

Cited by 12 publications

(6 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Disappointingly, however, all of the alcohol to azide protocols that were examined produced low yields and/or a partially racemized product, which could not be effectively upgraded at the azide or amine stage by recrystallization. The problem was further exacerbated by the resistance of several diastereomeric salts of the racemic, as well as the enantioenriched, amine to efficient upgrading . It was thus apparent that other stereopure precursors of the chiral amine had to be considered, which led us to carbamate derivatives.…”

Section: Resultsmentioning

confidence: 99%

1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives

Cividino

Delair

et al. 2006

J. Org. Chem.

View full text Add to dashboard Cite

The title compound has proven to be an excellent chiral auxiliary for nitrones in SmI2-mediated reductive coupling with alpha,beta-unsaturated esters. A variety of such nitrones, prepared from aldehydes and enantiopure N-hydroxy-1-(2,4,6-triisopropylphenyl)ethylamine, afforded gamma-N-hydroxyamino esters in high yields and diastereomeric purity. These adducts, readily available as either enantiomer, could be transformed into gamma-N-acetoxyamino esters, N-Boc-gamma-amino esters, and gamma-lactams.

show abstract

Section: Resultsmentioning

confidence: 99%

1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives

Cividino

Delair

et al. 2006

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…At the end A‐aza‐DA cycloaddtion of enantiopure imines, provided from enantiopure 1‐mesitylethylamine and aromatic aldehydes, with Danishefsky's diene was studied (Scheme ). As can be seen from Scheme , the reaction proceeded smoothly to afford the respective cycloaddition adduct 55 in high anti ‐selectivity …”

Section: Asymmetric Reaction Of Dainshefsky Dienes With Imines Derivementioning

confidence: 88%

Applications of Dainshefsky's Dienes in the Asymmetric synthesis of Aza‐Diels‐Alder Reaction

Koshvandi

Heravi

2018

The Chemical Record

View full text Add to dashboard Cite

Asymmetric hetero-Diels-Alder (AHDA) reactions provide a multitude of opportunities for the highly efficient, regio- and stereoselective construction of various heterocycles in enantiomerically pure form. The asymmetric aza-Diels-Alder (A-aza-DA) reaction using diversely hetero-dienophiles and hetero-dienes have been increasingly developed as a valuable method for the synthesis of functionalized nitrogen ring systems. The purpose of this review is to give a detailed discussion of the A-aza-DA reaction particularly, the stereoselective reactions of imines as dienophiles with Dainshefsky dienes to obtain optically pure aza-Diels-Alder products. The development of stereoselective variants of the reaction make use of imines as the dienophile and Dainshefsky dienes is at the forefront of these studies. This review updates the A-aza-DA reactions covering the literature from 1972 till date.

show abstract

“…Hashimoto, Saigo and co-workers 28 reported a new variation of the Kunz method, where they used a non-natural auxiliary to induce chirality during the aza-Diels-Alder reaction (Scheme 12). Aldimine 47, derived from enantiopure 1-(S)-methyl mesitylethylamine and aromatic aldehydes, reacted with Danishefsky's diene 39 in the presence BF 3 ÁEt 2 O, to afford 2,3-dihydro-4-pyridones 48 with high diastereoselectivity but moderate yield.…”

Section: Stereoselective Syntheses Of Cyclic Enaminonesmentioning

confidence: 99%

Cyclic enaminones. Part I: stereocontrolled synthesis using diastereoselective and catalytic asymmetric methods

Chattopadhyay

Hanessian

2015

Chem. Commun.

View full text Add to dashboard Cite

Cyclic enaminones are versatile intermediates to construct a variety of azacyclic frameworks and have been widely used in alkaloid synthesis. Here, we summarize three approaches for stereoselective syntheses of cyclic enaminones and their functionalized derivatives. These include chiral substrates (chirons) as starting materials, syntheses employing non-catalytic (stoichiometric) reagents, and catalytic asymmetric methods.

show abstract

A new non-natural chiral auxiliary: design, synthesis, and resolution of 1-mesitylethylamine and its application in the asymmetric aza-Diels–Alder reaction

Cited by 12 publications

References 24 publications

1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives

1-(2,4,6-Triisopropylphenyl)ethylamine: A New Chiral Auxiliary for the Asymmetric Synthesis of γ-Amino Acid Derivatives

Applications of Dainshefsky's Dienes in the Asymmetric synthesis of Aza‐Diels‐Alder Reaction

Cyclic enaminones. Part I: stereocontrolled synthesis using diastereoselective and catalytic asymmetric methods

Contact Info

Product

Resources

About