Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights-Reference-Cited by-同舟云学术

Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights

Published:2017 Issue:4 Volume:8 Page:2904-2913
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Orue Ane¹²³⁴,Uria Uxue¹²³⁴,Roca-López David⁵⁶⁷⁸⁴,Delso Ignacio⁹¹⁰⁷⁸⁴,Reyes Efraím¹²³⁴,Carrillo Luisa¹²³⁴^ORCID,Merino Pedro⁵⁶⁷⁸⁴,Vicario Jose L.¹²³⁴^ORCID

Affiliation:

1. Department of Organic Chemistry II

2. University of the Basque Country (UPV/EHU)

3. 48080 Bilbao

4. Spain

5. Departamento de Síntesis y Estructura de Biomoléculas

6. Instituto de Síntesis Química y Catálisis Homogénea (ISQCH)

7. Universidad de Zaragoza

8. CSIC

9. Servicio de Resonancia Magnética Nuclear

10. Centro de Química y Materiales de Aragón (CEQMA)

Abstract

Racemic 2-hydroxydihydropyran-5-ones react as unconventional O-pronucleophiles in a conjugate addition/Michael reaction cascade process under DKR, leading to the formation of a single stereoisomer out of 16 possible ones.

Funder

Euskal Herriko Unibertsitatea

Eusko Jaurlaritza

Ministerio de Economía y Competitividad

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2017/SC/C7SC00009J

Reference131 articles.

1. Catalytic Asymmetric Conjugate Reactions, ed. A. Cordova, Wiley-VCH, Weinheim, 2010