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Dive into the research topics where Richard H. Wallace is active.

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Featured researches published by Richard H. Wallace.


Tetrahedron Letters | 1992

Preparation and 1-carbon homologation of boronic ester substituted Δ2-isoxazolines: The 1,3 dipolar cycloaddition of nitrile oxides to vinyl boronic esters

Richard H. Wallace; K.K. Zong

Abstract The dipolar cycloaddition of a variety of nitrile oxides to pinacol vinylboronate ( 2 ) is described. In addition, the 1-carbon homologation of the boronic ester substituted Δ 2 -isoxazolines obtained from the cycloadditions has been carried out employing iodomethyllithium.


Tetrahedron Letters | 1997

An efficient method for the preparation of optically active 4-hydroxy-Δ2-isoxazolines

Richard H. Wallace; Jinchu Liu; K.K. Zong; Alicia Eddings

Abstract In this letter we report a method for the preparation of optically active 4-hydroxy-Δ 2 -isoxazolines. This methodology relies on the use of a camphorsultam substituted vinylboronic ester which upon nitrile oxide cycloaddition and oxidation affords the optically active 4-hydroxy-Δ 2 -isoxazolines in good yield.


Tetrahedron Letters | 1997

Sodium percarbonate: A multifunctional reagent for the preparation of optically active 4-hydroxy-Δ2-isoxazolines

Jinchu Liu; Alicia Eddings; Richard H. Wallace

Abstract In this letter we report a general method for the preparation of optically active 4-hydroxy-Δ2-isoxazolines. This one-pot method employs sodium percarbonate for nitrile oxide generation, oxidation of the intermediate boronic ester substituted Δ2-isoxazoline, and cleavage of the chiral auxiliary from the final product.


Tetrahedron Letters | 1994

A facile method for the preparation of 4-hydroxy-Δ2-isoxazolines via a cycloaddition/oxidation procedure employing nitrile oxides and vinylboronic esters

Richard H. Wallace; Jinchu Liu

Abstract The 1,3-dipolar cycloaddition of aromatic nitrile oxides with trans-1,2-disubstituted vinylboronic esters affords the 4-boronic ester substituted Δ2-isoxazoline as the major regioisomer. If the reaction mixture is treated with t-BuOOH the corresponding 4-hydroxy-Δ2-isoxazolines are obtained in good yield.


Journal of Organometallic Chemistry | 1999

The preparation of optically active boronic ester substituted Δ2-isoxazolines

Richard H. Wallace; K.K. Zong

Abstract In this paper we report our recent results in the area of nitrile oxide cycloaddition to optically active vinylboronic esters to afford optically active boronic ester substituted Δ 2 -isoxazolines. In these studies, a number of optically active diols were investigated and TADDOLs have been found to afford the best diastereoselectivity. The mixture of diastereomers obtained in these reactions can be readily purified by formation of the diethanolamine–boron complexes and recrystallized to afford the pure enantiomers.


Tetrahedron Letters | 1988

Dimeric products from the dissolving metal reduction of camphor

John W. Huffman; Richard H. Wallace; William T. Pennington

Abstract Various dissolving metal reductions of (+)-camphor afford one of two pinacols frequently accompanied by a dimeric product in which one bicycloheptane unit has been cleaved. Similar reductions of (±)-camphor afford various mixtures of (±)- exo - endo , (±)- endo - endo and meso endo - endo pinacols. The structures of two of these products were confirmed by X-ray crystallography.


Tetrahedron Letters | 1987

Dissolving metal reductions of ketones: comments on the dianion mechanism

John W. Huffman; Wen-Pang Liao; Richard H. Wallace

Abstract The reduction of (+)-camphor using Li, Na, and K in THF with sonication is reported. These reductions give the same results as those obtained in NH 3 . The mechanism of these reactions is discussed.


Synthetic Communications | 1995

The In Situ Generation and Use of Iodomethyllithium for the One-Carbon Homologation of Boronic Esters and Epoxide Formation from Carbonyl Compounds

Richard H. Wallace; William Battle

Abstract Iodomethyllithium is shown to be an effective reagent for the one-carbon homologation of oxygenated boronic esters. The use of iodomethyllithium for the preparation of pinacol iodomethaneboronate and for the synthesis of epoxides from carbonyl compounds is also discussed.


Journal of Chemical Education | 2006

A Quick and Easy Simplification of Benzocaine's NMR Spectrum

Suzanne R. Carpenter; Richard H. Wallace

The preparation of benzocaine is a common experiment used in sophomore-level organic chemistry. Its straightforward procedure and predictable good yields make it ideal for the beginning organic student. Analysis of the product via NMR spectroscopy, however, can be confusing to the novice interpreter. An inexpensive, quick, and effective method for simplifying the NMR spectrum is reported. The method results in a spectrum that is cleanly integrated and more easily interpreted.


Journal of Organic Chemistry | 1989

Some observations on the validity and generality of the "Cieplak stereoelectronic effect"

A. I. Meyers; Richard H. Wallace

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A. I. Meyers

Colorado State University

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K.K. Zong

University of Alabama

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Alicia Eddings

Armstrong State University

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Hyok-Boong Kwon

Colorado State University

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