Work

Enantioselective Synthesis of 2,2,5-Tri- and 2,2,5,5-Tetrasubstituted Tetrahydrofurans via [4 + 2] Cycloaddition and Ring-Opening Cross-Metathesis

Year: 2011

Type: article

Abstract: A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Diels-Alder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed into 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans, which are structural subunits of many natural products, via regioselective ring-opening metathesis/cross-metathesis or oxidative cleavage/refunctionalization.

Source: Organic Letters

DOI: 10.1021/ol102798f

Authors: Noah M. Benjamin, Stephen F. Martin

Institution: The University of Texas at Austin

Language: English

Topic: Synthetic Organic Chemistry Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, National Institutes of Health, National Institute of General Medical Sciences

Awards: G2469423531, Strategies for the Syntheses of Bioactive Targets