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 Medicine

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