Work

Stereocontrolled and time-honored access to piperidine- and pyrrolidine-fused 3-methylenetetrahydropyrans using lactam-tethered alkenols

Year: 2024

Type: article

Abstract: bromoetherification of the alkenols and concomitant elimination to arrive at the desired 3-MeTHPs. The methylene portion of the 3-MeTHP is unveiled at a late stage, which is noteworthy since all existing approaches to 3-MeTHPs rely on early-stage introduction of the methylene group. The second strategy involves transition metal-catalyzed alkoxylation of the tethered alkenol followed by base-induced double bond isomerization. The lactam-fused 3-MeTHPs are obtained in high site- and diastereo-selectivities. Post-modification of the bicycles has led to the construction of 3-MeTHP-fused saturated piperidines and pyrrolidines as well as 3-MeTHPs bearing four contiguous stereocenters.

Source: RSC Advances

DOI: 10.1039/d4ra04916k

Authors: Timothy K. Beng, Ifeyinwa S. Anosike, Jasleen Kaur

Institution: Central Washington University

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,042

Funder: Central Washington University