A Practical and Scaleable Synthesis of 1R,5S-Bicyclo[3.1.0]hexan-2-one: The Development of a Catalytic Lithium 2,2,6,6-Tetramethylpiperidide (LTMP) Mediated Intramolecular Cyclopropanation of (R)-1,2-Epoxyhex-5-ene

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2007-04-18 DOI:10.1021/op700042w

Anthony D. Alorati, Matthew M. Bio, Karel M. J. Brands, Ed Cleator, Antony J. Davies, Robert D. Wilson, Chris S. Wise

引用次数: 10

Abstract

An efficient synthesis of 1R,5S-bicyclo[3.1.0]hexan-2-one from (R)-1,2-epoxyhex-5-ene is described. Development of a catalytic intramolecular cyclopropanation of (R)-1,2-epoxyhex-5-ene gives the key homochiral bicycle[3.1.0]hexan-1-ol, which is then oxidized to the desired ketone. This process has been successfully demonstrated on a multi-kilogram scale.

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实用且可扩展的1R, 5s -双环[3.1.0]己烯-2 -1的合成:催化2,2,6,6-四甲基哌啶锂(LTMP)介导的(R)-1,2-环氧己烯-5-烯分子内环丙烷化反应的研究

以(R)-1,2-环氧己-5-烯为原料，高效合成了1R, 5s -双环[3.1.0]己-2-酮。(R)-1,2-环氧己烯-5-烯的分子内催化环丙烷化得到关键的同手性环[3.1.0]己烷-1-醇，然后被氧化成所需的酮。这个过程已经成功地在数公斤的尺度上进行了演示。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

期刊介绍： The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.