Gold(I)-Catalyzed Isomerization of Allenyl Carbinol Esters: An Efficient Access to Functionalized 1,3-Butadien-2-ol Esters
- 13 February 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (6) , 985-988
- https://doi.org/10.1021/ol063031t
Abstract
A study concerning the gold(I)-catalyzed rearrangement of diversely substituted allenyl carbinol esters into functionalized 1,3-butadien-2-ol esters is described. The mild conditions employed allow the efficient, rapid, and stereoselective synthesis of a variety of such compounds via a new 1,3-shift of an ester moiety onto a gold-activated allene.Keywords
This publication has 7 references indexed in Scilit:
- Gold(I) Catalyzed Isomerization of 5-en-2-yn-1-yl Acetates: An Efficient Access to Acetoxy Bicyclo[3.1.0]hexenes and 2-Cycloalken-1-onesJournal of the American Chemical Society, 2006
- Phosphine Gold(I) Bis-(trifluoromethanesulfonyl)imidate Complexes as New Highly Efficient and Air-Stable Catalysts for the Cycloisomerization of EnynesOrganic Letters, 2005
- A CONVENIENT AND SELECTIVE METHOD FOR PREPARATION OF ENOL ACETATES FROM KETONES USING MONTMORILLONITE KSF CLAYSynthetic Communications, 2002
- Synthesis of 13-Acetoxy-13-demethylretinal, Its Pigment Formation with Bacteriopsin, and Apparent Dark-Inactivating Effect on the PigmentThe Journal of Organic Chemistry, 1995
- Palladium-Assisted Heteroannulation of Acetoxy-1, 3-dienesSynthetic Communications, 1989
- Tailor-made butadienes for the site-selective cycloaddition with quinizarinquinone and other unsymmetrically substituted quinonesThe Journal of Organic Chemistry, 1985
- Arylation and 1-Alkenylation on α-Position of Ketones via Tributyltin Enolates Catalyzed by Palladium ComplexBulletin of the Chemical Society of Japan, 1984