How an early or late transition state impacts the stereoselectivity of tetrahydropyran formation by intramolecular oxa-Michael addition-Reference-Cited by-同舟云学术

How an early or late transition state impacts the stereoselectivity of tetrahydropyran formation by intramolecular oxa-Michael addition

Published:2019 Issue:25 Volume:17 Page:6293-6304
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Csókás Dániel¹²³⁴^ORCID,Ho Annabel Xuan Ying¹²³⁴,Ramabhadran Raghunath O.⁵⁶⁷⁸^ORCID,Bates Roderick W.¹²³⁴^ORCID

Affiliation:

1. Division of Chemistry and Biological Chemistry

2. School of Physical and Mathematical Sciences

3. Nanyang Technological University

4. Singapore

5. Indian Institute of Science Education and Research (IISER) Tirupati

6. Transit Campus – Sree Rama Engineering College

7. Tirupati – 517507

8. India

Abstract

Acid catalysis delivers the cis isomer as the kinetic product via a late transition state; base catalysis delivers the trans isomer via an early transition state.

Funder

Science and Engineering Research Board

Nanyang Technological University

Economic Development Board - Singapore

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2019/OB/C9OB00750D

Reference41 articles.

1. Recent application of oxa-Michael reaction in complex natural product synthesis

2. Strategies for the construction of tetrahydropyran rings in the synthesis of natural products

3. Total Synthesis of Tetrahydropyran-Containing Natural Products Exploiting Intramolecular Oxa-Conjugate Cyclization

4. Recent developments in the field of oxa-Michael reactions

5. Synthesis of six-membered oxygenated heterocycles through carbon–oxygen bond-forming reactions

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