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Updated: Jun 12, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

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在二醇的生物合成和下游加工方面的进展

Yongfei Liu1, Chijian Zhang2, An-Ping Zeng1

  • 1Center for Synthetic Biology and Integrated Bioengineering, Westlake University, Hangzhou 310030, Zhejiang, China; School of Engineering, Westlake University, Hangzhou 310030, Zhejiang, China; Zhejiang Provincial Key Laboratory of Intelligent Low-Carbon Biosynthesis, Hangzhou 310030, Zhejiang, China; Research Center for Industries of the Future, Westlake University, No. 600 Dunyu Road, 310030, Zhejiang Province, China.

Biotechnology advances
|September 21, 2024
PubMed
概括

本综述探讨了微生物对1,3-二醇 (PDO) 和二醇 (BDO) 等关键二醇的生产. 它强调了生物基二醇制造的代谢平台和下游加工.

关键词:
1,3-丁二醇的使用方法1,3-二醇的使用方法1,4-布坦二醇的使用方法迪奥尔 (Diol) 是一种下游加工是下游加工.代谢工程是代谢工程.合成生物学 合成生物学

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Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Aldehydes and Ketones with Water: Hydrate Formation

An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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