π-Facial selectivity in the Diels–Alder reaction of glucosamine-based chiral furans and maleimides-Reference-Cited by-同舟云学术

π-Facial selectivity in the Diels–Alder reaction of glucosamine-based chiral furans and maleimides

Published:2023 Issue:9 Volume:21 Page:1888-1894
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

van der Loo Cornelis H. M.¹^ORCID,Schim van der Loeff Rutger¹,Martín Avelino²,Gomez-Sal Pilar²^ORCID,Borst Mark L. G.³^ORCID,Pouwer Kees³,Minnaard Adriaan J.¹^ORCID

Affiliation:

1. Department of Chemical Biology, Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands

2. Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andres M. Del Rio” (IQAR), Universidad de Alcalá. Alcalá de Henares, 28805, Madrid, Spain

3. Symeres B.V., Kadijk 3, 9747 AT Groningen, The Netherlands

Abstract

Enantiopure glucosamine based furans were used to induce π-facial selectivity in the DA cycloaddition. High π-face selectivity, up to 6.5 : 1, was achieved and afforded oxanorbornene building blocks on multi gram scale in 58–59% yield.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/OB/D2OB02221D

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