Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins

Jian Wang; Hao Li; Wenhu Duan; Liansuo Zu; Wei Wang

doi:10.1021/ol0519137

Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins

Org Lett. 2005 Oct 13;7(21):4713-6. doi: 10.1021/ol0519137.

Authors

Jian Wang¹, Hao Li, Wenhu Duan, Liansuo Zu, Wei Wang

Affiliation

¹ Department of Chemistry, University of New Mexico, Albuquerque, New Mexico 87131-0001, USA.

PMID: 16209517
DOI: 10.1021/ol0519137

Abstract

[reaction: see text] A novel binaphthyl-derived amine thiourea organocatalyst has been developed and demonstrated to efficiently catalyze Michael addition reactions (using as low as 1 mol % loading) of diketones to nitroalkenes with remarkably high enantioselectivities.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Catalysis
Models, Molecular
Molecular Structure
Naphthalenes / chemistry*
Nitro Compounds / chemistry*
Pentanones / chemistry*
Stereoisomerism
Thiourea / chemistry*

Substances

Alkenes
Naphthalenes
Nitro Compounds
Pentanones
acetylacetone
Thiourea