Enantioselective Cycloaddition Reactions Catalyzed by BINOL-Derived Phosphoric Acids and N-Triflyl Phosphoramides: Recent Advances

Felix E Held; Dominik Grau; Svetlana B Tsogoeva

doi:10.3390/molecules200916103

Enantioselective Cycloaddition Reactions Catalyzed by BINOL-Derived Phosphoric Acids and N-Triflyl Phosphoramides: Recent Advances

Molecules. 2015 Sep 3;20(9):16103-26. doi: 10.3390/molecules200916103.

Authors

Felix E Held¹, Dominik Grau², Svetlana B Tsogoeva³

Affiliations

¹ Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials, University of Erlangen-Nürnberg, Henkestrasse 42, Erlangen 91054, Germany. [email protected].
² Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials, University of Erlangen-Nürnberg, Henkestrasse 42, Erlangen 91054, Germany. [email protected].
³ Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials, University of Erlangen-Nürnberg, Henkestrasse 42, Erlangen 91054, Germany. [email protected].

Abstract

Over the last several years there has been a huge increase in the development and applications of new efficient organocatalysts for enantioselective pericyclic reactions, which represent one of the most powerful types of organic transformations. Among these processes are cycloaddition reactions (e.g., [3+2]; formal [3+3]; [4+2]; vinylogous [4+2] and 1,3-dipolar cycloadditions), which belong to the most utilized reactions in organic synthesis of complex nitrogen- and oxygen-containing heterocyclic molecules. This review presents the breakthrough realized in this field using chiral BINOL-derived phosphoric acids and N-triflyl phosphoramide organocatalysts.

Keywords: BINOL-derived phosphoric acids; N-triflyl phosphoramides; cycloaddition reactions; enantioselective pericyclic reactions.

Publication types

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

MeSH terms

Catalysis
Cyclization
Molecular Structure
Phosphoramides / chemistry*
Phosphoric Acids / chemistry*

Substances

Phosphoramides
Phosphoric Acids