𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Cascade Reactions: Sequential Homobimetallic Catalysis Leading to Benzofurans and β,γ-Unsaturated Esters

✍ Scribed by Bartolo Gabriele; Raffaella Mancuso; Giuseppe Salerno; Mirco Costa

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
152 KB
Volume
348
Category
Article
ISSN
1615-4150

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The concatenation between a Pd(0)‐promoted deallylation catalytic cycle and a Pd(II)‐promoted heterocyclization catalytic cycle (an example of what we have named “sequential homobimetallic catalysis”) has been shown to occur starting from 1‐(2‐allyloxyphenyl)‐2‐yn‐1‐ols 1 to afford 2‐benzofuran‐2‐ylacetic esters 2 and β,γ‐unsaturated esters in high yields under carbonylative conditions. In view of the conceptual as well as the synthetic importance of the process, the mechanistic aspects and the synthetic scope of the reaction have been investigated in detail. All the experimental evidence is in agreement with the sequential homobimetallic mechanism, and the reaction has proven to be of general synthetic applicability.

📜 SIMILAR VOLUMES

Organocatalyzed Cascade Reactions of Cyc
Organocatalyzed Cascade Reactions of Cyclic β-Enamino Esters and α,β-Unsaturated Aldehydes Leading to Indoloquinolizidines and Benzoquinolizidines
✍ Xiaoyu Wu; Linlin Nie; Huihui Fang; Jie Chen; Weiguo Cao; Gang Zhao 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 545 KB

## Abstract Organocatalyzed cascade reactions between cyclic β‐enamino esters and α,β‐unsaturated aldehydes have been developed. They provide highly substituted indolo[2,3‐__a__]quinolizidines and benzo[__a__]quinolizidines in moderate to good yields and with good to excellent enantioselectivities.