Synthesis of 1-amino-2-phenylethane-1-boronic acid derivatives

Matteson, Donald S.; Sadhu, Kizhakethil Mathew

doi:10.1021/om00082a019

Cited by 103 publications

(96 citation statements)

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“…It was then recognized that lithiohexamethyldisilazane, LiN(SiMe 3 ) 2 , should provide the requisite primary amino substituent in protected form. This expectation proved correct, and desilylation to the (α-aminoalkyl)boronic acid proved feasible, provided the amino function was promptly protected by acylation or protonation [62,63]. Free amino boronic esters such as 116 rearranged to the hydrolytically unstable N-borylamine (117) within a few hours (Scheme 8.27).…”

Section: Amino and Amido Substituentsmentioning

confidence: 98%

(α‐Haloalkyl)boronic Esters in Asymmetric Synthesis

Matteson¹

2005

Boronic Acids

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The utility of (α-haloalkyl)boronic esters in asymmetric synthesis results from a unique combination of several features of their chemistry. A wide variety of products can be obtained in very high stereopurity, and the reactions are compatible with a considerable variety of functional substituents, provided that OH and NH groups are masked. Stereospecific displacement of halide from an (α-haloalkyl)boronic ester with a nucleophile yields an asymmetric boronic ester, which can either be converted stereospecifically into another product such as an alcohol or put into another cycle of reaction with (dihalomethyl)lithium to install additional stereocenters. The general synthetic utility of these boronic esters can best be understood from a detailed outline of the general processes involved.The most useful biological applications of these compounds have included the synthesis of some asymmetric insect pheromones in very high stereopurity, described in Sections 8.3.1 and 8.3.3, and the proteasome inhibitor "Velcade™" (bortezomib) developed by Millennium Pharmaceuticals and recently approved by the United States FDA as well as the European Union for treatment of relapsed and refractory multiple myeloma, Section 8.3.6. General Description of (α-Haloalkyl)boronic Ester Chemistry A Brief History of Boronic Ester ChemistryFirst, simple achiral boronic acids and esters are readily available from various sources (Chapter 1). The first synthesis from an organozinc reagent preceded general acceptance of Avogadro's hypothesis [1], and was superseded nearly a century ago by the now standard preparation from Grignard reagents [2,3]. Hydroboration has Boronic Acids. Edited by Dennis G. Hall

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Section: Amino and Amido Substituentsmentioning

confidence: 98%

(α‐Haloalkyl)boronic Esters in Asymmetric Synthesis

Matteson¹

2005

Boronic Acids

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“…Crystal structural analyses of the enzyme complexes with different inhibitors showed that there were very noticeable differences in the P2 pocket. Therefore, a series of β,β-dialkylphenethylglycine P2 analogs of DuP-714 (14) were designed and synthesized. These compounds, such as 15 and 16, showed greater selectivity for thrombin over factor I and improved safety profile [61].…”

Section: Protease Inhibitors That Bind To One Side Of the Active Sitementioning

confidence: 99%

“…This enabled the synthesis of many potent boronic acid-based enzyme inhibitors. Thereafter, several variations of the general route have been developed and used for these synthesis of different kinds of enzyme inhibitors [13][14][15][16][17]. The development of the synthetic methodologies is discussed in detail in Chapter 8, and therefore will not be duplicated here.…”

Section: Introductionmentioning

confidence: 99%

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Biological and Medicinal Applications of Boronic Acids

Yang¹,

Gao

Wang

2005

Boronic Acids

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“…It is known that primary and secondary derivatives of α-aminoboronic acids are not stable in their neutral form; however, they can be stabilized either by forming their hydrochloride salts or by converting the molecules into their amide derivatives. [4][5][6] In this context, new effective methods to prepare amino and related boron compounds will have a tremendous impact on synthetic, bioinorganic, and pharmaceutical chemistry. [7][8][9][10][11][12] The first synthesis of an α-amidoboronic ester was reported by Matteson et al, [13] and remains the standard method for synthesis of α-aminoboronic acids; however, it is a multistep method and is time consuming.…”

Section: Introductionmentioning

confidence: 99%