A readily available and bench-stable cyanomethyl sulfonium salt was used in highly diastereoselective Corey-Chaykovsky cyclopropanation reactions of electron-poor olefins. This efficient method provides a rapid route to access densely functionalized cyclopropyl nitriles.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8cc05602a | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthetic Efforts toward Lannotinidine G Based on an Aziridinium-Mediated Ring Contraction and Dienyne Metathesis.
Org Lett
April 2024
Department of Chemistry, New York University, New York, New York 10003, United States.
Lannotinidine G is a unique Lycopodium alkaloid that features a tricyclic [6/6/6] core with 3 contiguous stereocenters and a 1,3-diene moiety in addition to a 7-membered lactone. Herein, we disclose our efforts toward the synthesis of this natural product, which achieved the construction of the aza-tricyclic core with the correct configuration at its three stereocenters. Key features of our strategy include a highly diastereoselective Fráter-Seebach alkylation and Corey-Chaykovsky type epoxide formation, an unusual aziridinium-mediated ring contraction for the formation of the piperidine moiety, and a regioselective dienyne metathesis.
View Article and Find Full Text PDFAn α-chloroaldehyde-based formal synthesis of eribulin.
Nat Commun
April 2023
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
Eribulin (Halaven) is the most structurally complex non-peptidic drug made by total synthesis and has challenged preconceptions of synthetic feasibility in drug discovery and development. However, despite decades of research, the synthesis and manufacture of eribulin remains a daunting task. Here, we report syntheses of the most complex fragment of eribulin (C14-C35) used in two distinct industrial routes to this important anticancer drug.
View Article and Find Full Text PDFDiastereoselective synthesis of new zwitterionic bicyclic lactams, scaffolds for construction of 2-substituted-4-hydroxy piperidine and its pipecolic acid derivatives.
RSC Adv
January 2022
Centro de QuííInstituto de Cienciasmica, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla Edif. IC-9 Complejo de Ciencias C.U. 72570 Puebla Mexico
The synthesis of new chiral highly functionalized zwitterionic bicyclic lactams starting from acyclic β-enaminoesters derived from ()-(-)-2-phenylglycinol is described. The key step involved an intramolecular non-classical Corey-Chaykovsky ring-closing reaction of the corresponding sulfonium salts derived from β-enaminoesters. This methodology permits the generation of two or three new stereogenic centers with high diastereoselectivity.
View Article and Find Full Text PDFOne-Pot Double Intramolecular Cyclization Approach to Tetralin-Based Cis-Fused Tetracyclic Compounds.
J Org Chem
April 2022
Department of Chemical Sciences, Tezpur University, Napaam, Sonitpur, Assam 784028, India.
Presented herein is a BF·OEt-mediated, diastereoselective one-pot double cyclization of 4-aryl-2-[(arylthio)methyl]butanals leading to the formation of -tetrahydro-6-naphtho[2,1-]thiochromenes for the first time. Mechanistically, the formation of the title products involves the one-pot intramolecular Friedel-Crafts hydroxyalkylation/intramolecular Friedel-Crafts alkylation cascade. This synthetic methodology is featured by its high atom economy, broad substrate scope, mild transition-metal-free reaction conditions, capability to assemble two new rings in one pot, and moderate to high yields (up to 94% yield).
View Article and Find Full Text PDFAsymmetric Sequential Corey-Chaykovsky Cyclopropanation/Cloke-Wilson Rearrangement for the Synthesis of 2,3-Dihydrofurans.
Org Lett
November 2021
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
The first sequential Corey-Chaykovsky cyclopropanation/Cloke-Wilson rearrangement between propargyl sulfonium salts and acrylonitrile derivatives has been developed, affording the tetra-substituted 2,3-dihydrofurans in generally excellent yields (57-98%) with good diastereoselectivities (7:1-18:1). In addition, chiral propargyl sulfonium salt is also suitable for this strategy, giving the optically active 2,3-dihydrofurans with good enantioselectivities. This reaction sequence was designed upon in situ generated 10π-conjugated structures from the dearomatization of indole fragments and subsequent intramolecular 1,6-addition.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!