The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction-Reference-Cited by-同舟云学术

The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction

Published:2022 Issue:2 Volume:20 Page:329-333
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Rehman Mintu¹^ORCID,Surendran Sravya¹^ORCID,Siddavatam Nagendra¹^ORCID,Rajendar Goreti¹^ORCID

Affiliation:

1. 2204, School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram, Vithura, Kerala, 695551, India

Abstract

Enhanced E-selectivity of olefins in Julia-Kocienski reaction of aldehydes with α-coordinating groups is demonstrated using TBAB. A systematic study is presented to show the chelation effect and size of the protecting group on E/Z-selectivity.

Funder

Science and Engineering Research Board

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/OB/D1OB02126E

Reference31 articles.

1. S. E.Kelly , Alkene Synthesis , in Comprehensive Organic Synthesis , ed. B. M. Trost and I. Fleming , Pergamon , Oxford , 1991 , vol. 1 , pp. 729–817

2. Syntheses a l'aide de sulfones v(+)- methode de synthese generale de doubles liaisons.

3. Julia–Kocienski olefination: a key reaction for the synthesis of macrolides

4. Mechanistic Manifold and New Developments of the Julia–Kocienski Reaction

5. The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds

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