Work

TiCl4-Promoted Tandem Carbonyl or Imine Addition and Friedel–Crafts Cyclization: Synthesis of Benzo-Fused Oxabicyclooctanes and Nonanes

Year: 2012

Type: article

Abstract: A new and convenient synthesis of benzo-fused 8-oxabicyclo[3.2.1]octane and 9-oxabicyclo[4.2.1]nonane derivatives are described. The reaction involved a TiCl(4)-mediated tandem carbonyl or imine addition followed by a Friedel-Crafts cyclization to provide these functionalized derivatives in good to excellent yields and high diastereoselectivity.

Source: Organic Letters

DOI: 10.1021/ol300494q

Authors: Arun K. Ghosh, Cuthbert D. Martyr, Chun-Xiao Xu

Institution: Purdue University West Lafayette

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Design & Synthesis of Nonpeptide Protease Inhibitors