Catalytic Enantioselective Intermolecular Cycloaddition of 2-Diazo-3,6-diketoester-Derived Carbonyl Ylides with Alkynes and Styrenes Using Chiral Dirhodium(II) Carboxylates

Dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, is an exceptionally effective catalyst for enantioselective tandem carbonyl ylide formation−cycloaddition reactions of 2-diazo-3,6-diketoesters with arylacetylene, alkoxyacetylene, and styrene dipolarophiles, providin...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2008-08, Vol.10 (16), p.3603-3606
Hauptverfasser:	Shimada, Naoyuki, Anada, Masahiro, Nakamura, Seiichi, Nambu, Hisanori, Tsutsui, Hideyuki, Hashimoto, Shunichi
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes - chemistry Azo Compounds - chemistry Carboxylic Acids - chemistry Catalysis Cyclization Epoxy Compounds - chemical synthesis Epoxy Compounds - chemistry Esters - chemistry Ketones - chemistry Molecular Structure Organometallic Compounds - chemistry Rhodium - chemistry Stereoisomerism Styrenes - chemistry
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	Dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, is an exceptionally effective catalyst for enantioselective tandem carbonyl ylide formation−cycloaddition reactions of 2-diazo-3,6-diketoesters with arylacetylene, alkoxyacetylene, and styrene dipolarophiles, providing cycloadducts in good to high yields and with enantioselectivities of up to 99% ee as well as with perfect exo diastereoselectivity for styrenes.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol8013733