Catalytic Asymmetric [4 + 2] Additions with Aliphatic Nitroalkenes

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2011 Dec 17

PMID 22174973

Citations 7

Authors

Keith J Bartelson

Ravi P Singh

Bruce M Foxman

Li Deng

Affiliations

Soon will be listed here.

Abstract

We describe an unprecedented cycloaddition reaction of 2-pyrones with aliphatic nitroalkenes catalyzed by a new bifunctional cinchona alkaloid-derived catalyst bearing a bulky TIPS-ether at the 9-position. The [2.2.2] bicyclic adducts were obtained in good yield with excellent diastereo- and enantioselectivity. Carbon isotope effects were measured by (13)C NMR and are indicative of a stepwise mechanism. Finally, a synthetic application is demonstrated, highlighting the utility of the cycloadducts.

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