Organocatalytic One-pot 1,4-/1,6-/1,2-addition Sequence for the Stereocontrolled Formation of Six Consecutive Stereocenters

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2015 Jan 8

PMID 25563802

Citations 2

Authors

Pankaj Chauhan

Suruchi Mahajan

Gerhard Raabe

Dieter Enders

Affiliations

Soon will be listed here.

Abstract

An unprecedented stereoselective organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence between β-dicarbonyl compounds, β-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed. The protocol opens an efficient entry to isoxazole bearing cyclohexanes with six consecutive stereogenic centers including one tetrasubstituted carbon in good yields and excellent diastereo- and enantioselectivities.

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