TY - JOUR
T1 - Gold-Catalyzed Amide/Carbamate-Linked N, O-Acetal Formation with Bulky Amides and Alcohols
AU - Ohsawa, Kosuke
AU - Ochiai, Shota
AU - Kubota, Junya
AU - Doi, Takayuki
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant Number JP19K16310 (Early-Career Scientists) and 15H05837 (Middle Molecular Strategy). This work was partially supported by the Platform Project for Supporting in Drug Discovery and Life Science Research from AMED under Grant Numbers JP20am0101095 and JP20am0101100.
Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.
PY - 2021/1/1
Y1 - 2021/1/1
N2 - A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.
AB - A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.
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U2 - 10.1021/acs.joc.0c02640
DO - 10.1021/acs.joc.0c02640
M3 - Article
AN - SCOPUS:85099168812
SN - 0022-3263
VL - 86
SP - 1281
EP - 1291
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -