Organocatalytic Enantioselective Vinylcyclopropane‐Cyclopentene (VCP‐CP) Rearrangement

Author:

Garay Gorka1,Hurtado Josebe1,Pedrón Manuel2,García Lorena13,Reyes Efraim1ORCID,Sánchez‐Díez Eduardo13,Tejero Tomás4,Carrillo Luisa1,Merino Pedro2,Vicario Jose L.1ORCID

Affiliation:

1. Department of Organic and Inorganic Chemistry University of the Basque Country (UPV/EHU) P.O. Box 644 48080 Bilbao Spain

2. Instituto de Biocomputación y Física de Sistemas Complejos (BIFI) Universidad de Zaragoza 50009 Zaragoza Spain

3. Current Address: Centre for Cooperative Research on Alternative Energies (CIC Energigune) Basque Research and Technology Alliance (BRTA) Alava Technology Park Vitoria-Gasteiz Spain

4. Instituto de Síntesis Química y Catálisis Homogénea (ISQH) Universidad de Zaragoza CSIC 50009 Zaragoza Spain

Abstract

AbstractWe have demonstrated that the catalytic and enantioselective vinylcyclopropane‐cyclopentene rearrangement can be carried out on (vinylcyclopropyl)acetaldehydes through activation via enamine intermediates. The reaction makes use of racemic starting materials that, upon ring opening facilitated by the catalytic generation of a donor‐acceptor cyclopropane, deliver an acyclic iminium ion/dienolate intermediate in which all stereochemical information has been deleted. The final cyclization step forms the rearrangement product, showing that chirality transfer from the catalyst to the final compound is highly effective and leads to the stereocontrolled formation of a variety of structurally different cyclopentenes.

Funder

Ministerio de Ciencia e Innovación

Eusko Jaurlaritza

Gobierno de Aragón

Publisher

Wiley

Subject

General Chemistry,Catalysis

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3