Issue 24, 2016
From the journal:

Organic & Biomolecular Chemistry

Lewis acid-promoted [2 + 2] cycloadditions of alkenes with aryl ketenes†

E. M. Rigsbee,‡a   C. Zhou,‡b   C. M. Rasik,b   A. Z. Spitz,c   A. J. Nicholsd  and  M. K. Brown*b  

* Corresponding authors

a SSCI, A Division of Albany Molecular Research Inc, 3065 Kent Avenue West Lafayette, IN 47906-1076, USA

b Indiana University, Department of Chemistry, 800 E. Kirkwood Ave, Bloomington, IN 47405, USA
E-mail: brownmkb@indiana.edu

c Albert Einstein College of Medicine, 1300 Morris Park Ave, Bronx, NY 10461, USA

d Eli Lilly and Co., 307 Merrill St., Indianapolis, IN, USA

Abstract

A method for the [2 + 2] cycloaddition of aryl ketenes and alkenes is presented. The process involves the in situ generation of a ketene in the presence of a Lewis acid. The utility of products is demonstrated towards the synthesis of a common scaffold found in several natural product families.

Graphical abstract: Lewis acid-promoted [2 + 2] cycloadditions of alkenes with aryl ketenes

  • This article is part of the themed collection: New Talent
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Article information

DOI
https://doi.org/10.1039/C5OB01837D
Article type
Communication
Submitted
02 set 2015
Accepted
22 set 2015
First published
30 set 2015

Org. Biomol. Chem., 2016,14, 5477-5480

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Lewis acid-promoted [2 + 2] cycloadditions of alkenes with aryl ketenes

E. M. Rigsbee, C. Zhou, C. M. Rasik, A. Z. Spitz, A. J. Nichols and M. K. Brown, Org. Biomol. Chem., 2016, 14, 5477 DOI: 10.1039/C5OB01837D

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