A Catalytic Highly Enantioselective Synthesis of Spirooxazolines

Oxidative Dearomatization ◽

Synthetic Utility ◽

Substituted Benzamides

A catalytic highly enantioselective synthesis of spirooxazolines is presented. Starting from readily available 2-naphthol-substituted benzamides and using catalytic amounts of a chiral triazole-substituted iodoarene catalyst, a variety of spirooxazolines can be isolated through an enantioselective oxidative dearomatization in up to 92% yield and 97% ee. The further synthetic utility of the optically enriched spirooxazolines was examined providing a corresponding 2-naphthalenole and an oxepin.<br>

Merging Oxidative Dearomatization and Aminocatalysis: One-Pot Enantioselective Synthesis of Tricyclic Architectures

Organic Letters ◽

10.1021/ol402546h ◽

2013 ◽

Vol 15 (22) ◽

pp. 5642-5645 ◽

Cited By ~ 50

Author(s):

François Portalier ◽

Flavien Bourdreux ◽

Jérôme Marrot ◽

Xavier Moreau ◽

Vincent Coeffard ◽

...

Keyword(s):

One Pot ◽

ChemInform Abstract: Enantioselective Synthesis of Bicyclo[2.2.2]octenones Using a Copper-Mediated Oxidative Dearomatization/[4 + 2] Dimerization Cascade.

ChemInform ◽

10.1002/chin.200829066 ◽

2008 ◽

Vol 39 (29) ◽

Author(s):

Suwei Dong ◽

Jianglong Zhu ◽

John A. Jr. Porco

Keyword(s):

Organocatalytic, Enantioselective Synthesis of Cyclohexadienone Containing Hindered Spirocyclic Ethers through an Oxidative Dearomatization/Oxa-Michael Addition Sequence

Angewandte Chemie ◽

10.1002/ange.201607039 ◽

2016 ◽

Vol 128 (48) ◽

pp. 15339-15343 ◽

Cited By ~ 9

Author(s):

Reddy Rajasekhar Reddy ◽

Satish Sonbarao Gudup ◽

Prasanta Ghorai

Keyword(s):

Michael Addition ◽

Application of Chiral Triazole-Substituted Iodoarenes in the Enantioselective Construction of Spirooxazolines

Chemical Communications ◽

10.1039/d1cc03246a ◽

2021 ◽

Author(s):

Ayham H Abazid ◽

Boris Johannes Nachtsheim

Keyword(s):

Substituted Benzamides

A catalytic highly enantioselective synthesis of spirooxazolines is presented. Starting from readily available 2-naphthol-substituted benzamides and using catalytic amounts of a chiral triazole-substituted iodoarene catalyst, a variety of spirooxazolines can...

Enantioselective Synthesis of Bicyclo[2.2.2]octenones Using a Copper-Mediated Oxidative Dearomatization/[4 + 2] Dimerization Cascade1

Journal of the American Chemical Society ◽

10.1021/ja711018z ◽

2008 ◽

Vol 130 (9) ◽

pp. 2738-2739 ◽

Cited By ~ 104

Author(s):

Suwei Dong ◽

Jianglong Zhu ◽

John A. Porco

Keyword(s):

Base-free enantioselective SN2 alkylation of 2-oxindoles via bifunctional phase-transfer catalysis

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.17.146 ◽

2021 ◽

Vol 17 ◽

pp. 2287-2294

Author(s):

Mili Litvajova ◽

Emiliano Sorrentino ◽

Brendan Twamley ◽

Stephen J Connon

Keyword(s):

Hydrogen Bond ◽

Ad Hoc ◽

Phase Transfer Catalysis ◽

Phase Transfer ◽

Quaternary Ammonium Salts ◽

Ammonium Salts ◽

Synthetic Utility ◽

First Time ◽

Derivatives Of

N-Protected oxindole derivatives of unprecedented malleability bearing ester moieties at C-3 have been shown to participate in enantioselective phase-transfer-catalysed alkylations promoted by ad-hoc designed quaternary ammonium salts derived from quinine bearing hydrogen-bond donating substituents. For the first time in such phase-transfer-catalysed enolate alkylations, the reactions were carried out under base-free conditions. It was found that urea-based catalysts outperformed squaramide derivatives, and that the installation of a chlorine atom adjacent to the catalyst’s quinoline moiety aided in avoiding selectivity-reducing complications related to the production of HBr in these processes. The influence of steric and electronic factors from both the perspective of the nucleophile and electrophile were investigated and levels of enantiocontrol up to 90% ee obtained. The synthetic utility of the methodology was demonstrated via the concise enantioselective synthesis of a potent CRTH2 receptor antagonist.