Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes – a reaction at the ‘oxonium-Prins’ vs. ‘ortho-quinone methide cycloaddition’ mechanistic nexus-Reference-Cited by-同舟云学术

Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes – a reaction at the ‘oxonium-Prins’ vs. ‘ortho-quinone methide cycloaddition’ mechanistic nexus

Published:2019 Issue:2 Volume:10 Page:406-412
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Nielsen Christian D.-T.¹²³⁴^ORCID,Mooij Wouter J.¹²³⁴^ORCID,Sale David⁵⁶⁷⁴^ORCID,Rzepa Henry S.¹²³⁴^ORCID,Burés Jordi⁸⁹¹⁰⁴^ORCID,Spivey Alan C.¹²³⁴^ORCID

Affiliation:

1. Department of Chemistry

2. Imperial College London

3. London

4. UK

5. Process Studies Group

6. Syngenta

7. Bracknell

8. School of Chemistry

9. University of Manchester

10. Manchester

Abstract

Herein we report a combined experimental and computational investigation of the acid catalyzed cyclocondensation reaction between styrenyl homoallylic alcohols and salicylaldehyde to form furanochromanes.

Funder

Syngenta International

Research Executive Agency

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2019/SC/C8SC04302G

Reference53 articles.

1. Stereoselective Reactions of ortho-Quinone Methide and ortho-Quinone Methide Imines and Their Utility in Natural Product Synthesis

2. o-Quinone methides: intermediates underdeveloped and underutilized in organic synthesis