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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.6K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.6K
Polymer Classification: Stereospecificity01:26

Polymer Classification: Stereospecificity

3.4K
Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
3.4K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

18.0K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
18.0K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

12.3K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
12.3K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

4.3K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.3K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

5.2K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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ストレンスリリースヘテロアトム機能化:開発,範囲,およびステレオ特異性

Justin M Lopchuk1, Kasper Fjelbye1, Yu Kawamata1

  • 1Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society
|February 1, 2017
PubMed
まとめ

薬剤化学者は,新しいストレンスリリース戦略を使用して,薬剤発見にビサイクロ[1.1.1]ペンタンのようなストレンスリングを簡単にインストールできます. この方法は"任意の段階"の機能化を行い,複雑な分子の合成を簡素化します.

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科学分野:

  • 有機化学
  • 薬剤化学
  • 薬物の発見

背景:

  • 薬物の発見は,新しい化学空間を探索するために,ますますストレートされたバイオアイソステル (例えば,ビサイクロ[1.1.1]ペンタン,アゼチジン,サイクロブタン) を利用しています.
  • これらの圧縮された断片を組み込むという合成的な課題は,しばしば鉛化合物の改変においてその応用を妨げます.

研究 の 目的:

  • 小規模でストレートなリングシステムの容易な"任意の段階"の設置のための一般的な戦略を開発する.
  • ストレートリングでヘテロアトムを機能させるための新しいステレオ特異的なストレートリリース反応を導入する.

主な方法:

  • 核愛者と反応するスプリングロードのC-CとC-N結合を利用する一般的な戦略の開発.
  • 方法論の適用は,小型の構成要素,後期的な中間物質,生物結合,およびペプチドのラベル付け.
  • 4つの新しいキラル"cyclopentylation"試薬の合成と特徴付け

主要な成果:

  • ストレートリングの"任意の段階"の設置が実証され,以前の合成の障害を克服しました.
  • アミン,アルコール,チオール,カルボキシル酸の最初のステレオ特異的なストレス解離機能化を達成した.
  • 生物結合とペプチドのラベリングに成功しました.

結論:

  • 開発されたストレイン・リリースの戦略は,医療化学におけるストレインリングを組み込むための汎用的かつ効率的な方法を提供します.
  • このアプローチは,薬剤発見と化学生物学アプリケーションのための合成バイオイソステルのアクセシビリティを大幅に拡大します.