从终端和化物中构建同质醇,并安装合成立体化学
Tomoya Miura1, Yui Nishida, Masahiro Murakami
1Department of Synthetic Chemistry and Biological Chemistry, Kyoto University , Katsura, Kyoto 615-8510, Japan.
一种新的 (((I) 催化剂将基基酸盐转化为基酸盐. 这种中间体与化物反应,以立体选择性地产生有价值的同同类醇.
科学领域:
- 有机金属化学 有机金属化学
- 有机合成 有机合成
背景情况:
- 基酸盐是多功能合成中间体.
- 同样性醇的立体选择性合成在有机化学中至关重要.
研究的目的:
- 开发一种新的催化方法来产生基酸.
- 为了实现同同类醇的立体选择性合成.
主要方法:
- 从终端基中制备2--1-基基酸盐.
- 使用阴离子 ((I) 复合物的催化.
- 核性添加生成的阿利博酸到化物中.
主要成果:
- ((I) 催化剂有效地将基基酸盐转化为基酸盐物种.
- 甲酸经历了立即的,立体选择性的核性添加到化物.
- 反应产生具有高立体选择性的同同类醇.
结论:
- 已经建立了一个用于合成同同醇醇的新催化途径.
- 这种方法提供了一个立体选择性路线,使用易于获得的起始材料.
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相关概念视频
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
