Asymmetric generation of fluorine-containing quaternary carbons adjacent to tertiary stereocenters: uses of fluorinated methines as nucleophiles

Xiao Han; Jie Luo; Chen Liu; Yixin Lu

doi:10.1039/b823184b

Asymmetric generation of fluorine-containing quaternary carbons adjacent to tertiary stereocenters: uses of fluorinated methines as nucleophiles

Chem Commun (Camb). 2009 Apr 21:(15):2044-6. doi: 10.1039/b823184b. Epub 2009 Feb 26.

Authors

Xiao Han¹, Jie Luo, Chen Liu, Yixin Lu

Affiliation

¹ Department of Chemistry, National University of Singapore, Singapore, Republic of Singapore.

PMID: 19333485
DOI: 10.1039/b823184b

Abstract

Organocatalytic asymmetric Michael reactions of fluorinated nucleophiles with nitroolefins catalyzed by Cinchona alkaloid-derived thiourea catalysts generated the desired Michael products containing vicinal fluorinated quaternary and tertiary chiral centers with exceptional enantioselectivity.

Publication types

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

MeSH terms

Alkenes / chemistry
Carbon / chemistry*
Catalysis
Cinchona Alkaloids / chemistry
Fluorine / chemistry*
Halogenation
Nitrogen Compounds / chemistry
Stereoisomerism
Thiourea / chemistry
Thiourea / isolation & purification

Substances

Alkenes
Cinchona Alkaloids
Nitrogen Compounds
Fluorine
Carbon
Thiourea