Preparation of a Storable Zinc Carbenoid Species and Its Application in Cyclopropanation, Chain Extension, and [2,3]-Sigmatropic Rearrangement Reactions

2010 ◽  
Vol 75 (4) ◽  
pp. 1244-1250 ◽  
Author(s):  
Arnaud Voituriez ◽  
Lucie E. Zimmer ◽  
André B. Charette
Keyword(s):  
Sigmatropic Rearrangement ◽  
Chain Extension ◽  
Rearrangement Reactions ◽  
Zinc Carbenoid

Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4348-4358 ◽  
Author(s):  
Fang Li ◽  
Feifei He ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Sigmatropic Rearrangement ◽  
Tertiary Amines ◽  
Amino Esters ◽  
Catalyst Free ◽  
Rearrangement Reaction ◽  
Rearrangement Reactions ◽  
Free Ammonium

The rearrangement reaction of ammonium ylides furnishes valuable α,α-disubstituted amino esters. In this work, we describe the visible-light photolysis reaction of aryldiazoacetates in the presence of tertiary amines that react via a free ammonium ylide in a sigmatropic rearrangement reaction to provide amino esters in moderate to very good yields (33 examples, up to 97% yield).

scholarly journals Stereoselective Formation of a Functionalized Dipeptide Isostere by Zinc Carbenoid-Mediated Chain Extension†

2009 ◽  
Vol 74 (2) ◽  
pp. 645-651 ◽  
Author(s):  
Weimin Lin ◽  
Cory R. Theberge ◽  
Timothy J. Henderson ◽  
Charles K. Zercher ◽  
Jerry Jasinski ◽  
...  
Keyword(s):  
Chain Extension ◽  
Zinc Carbenoid

A New Class of Ammonium Ylid for [2,3]-Sigmatropic Rearrangement Reactions: ene-endo-Spiro Ylids

2005 ◽  
Vol 7 (10) ◽  
pp. 2075-2078 ◽  
Author(s):  
Edward Roberts ◽  
Julien P. Sançon ◽  
J. B. Sweeney
Keyword(s):  
Sigmatropic Rearrangement ◽  
New Class ◽  
Rearrangement Reactions

Formation of β-Substituted γ-Keto Esters via Zinc Carbenoid Mediated Chain Extension

Synthesis ◽  
2007 ◽  
Vol 2007 (15) ◽  
pp. 2404-2408 ◽  
Author(s):  
Charles Zercher ◽  
Weimin Lin ◽  
Robert McGinness ◽  
Emerald Wilson
Keyword(s):  
Chain Extension ◽  
Keto Esters ◽  
Zinc Carbenoid

Regioselective [5,5]-Sigmatropic Rearrangement Reactions of Aryl Hydrazides

2006 ◽  
Vol 8 (10) ◽  
pp. 2047-2050 ◽  
Author(s):  
Hong-Min Kang ◽  
Young-Kwan Lim ◽  
In-Jee Shin ◽  
Hee-Yeon Kim ◽  
Cheon-Gyu Cho
Keyword(s):  
Sigmatropic Rearrangement ◽  
Rearrangement Reactions

Zinc carbenoid-mediated chain extension of β-keto amides

Tetrahedron ◽  
2001 ◽  
Vol 57 (42) ◽  
pp. 8793-8800 ◽  
Author(s):  
Ramona Hilgenkamp ◽  
Charles K Zercher
Keyword(s):  
Chain Extension ◽  
Zinc Carbenoid
Sign in / Sign up

Export Citation Format

Share Document