Acid-catalyzed intramolecular ring-opening reactions of cyclopropanated oxabenzonorbornadienes with alcohol nucleophiles

2019 ◽  
Vol 60 (45) ◽  
pp. 151228 ◽  
Author(s):  
Christopher Wicks ◽  
Samuel Koh ◽  
Austin Pounder ◽  
Emily Carlson ◽  
William Tam
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Acid Catalyzed ◽  
Intramolecular Ring

Acid-Catalyzed Intramolecular Ring-Opening Reactions of Cyclopropanated Oxabenzonorbornadienes with Carboxylic Acid Nucleophiles

Synthesis ◽  
2021 ◽  
Author(s):  
Angel Ho ◽  
Austin Pounder ◽  
Samuel Koh ◽  
Matthew Macleod ◽  
Emily Carlson ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Ring Opening ◽  
Reaction Conditions ◽  
Ring Opening Reactions ◽  
Acidic Conditions ◽  
Acid Catalyzed ◽  
Type 3 ◽  
Intramolecular Ring

The present work demonstrates the ability of carboxylic acid-tethered cyclopropanated oxabenzonorbornadienes (CPOBDs) to undergo ring-opening reactions in mild acidic conditions. The optimized reaction conditions involve the use of pTsOH in DCE at 90 °C. Two regioisomers are formed but the reactions are highly regioselective towards type 3 ring-opened products. It was observed that substitution at the C-5 and aryl positions of CPOBD significantly hinders the ring opening reactions leading to decreased yields of ring-opened product, although high regioselectivity for the Type 3 ring-opened product is still maintained. Herein, we report the first examples of acid-catalyzed intramolecular ring-opening reactions of CPOBD with carboxylic acid nucleophiles.

scholarly journals Acid Catalyzed Ring Opening Reactions of 6-Deoxy-9-deoxo-9a-aza-9a-homoerythromycin A 6,9-Cyclic Imino Ether.

1998 ◽  
Vol 51 (9) ◽  
pp. 893-896 ◽  
Author(s):  
GORJANA LAZAREVSKI ◽  
GABRIJELA KOBREHEL ◽  
AMALIJA NARANDA ◽  
ZRINKA BANIC-TOMIŠIC ◽  
BISERKA METELKO
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Acid Catalyzed
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