Directing Group Assisted Nucleophilic Substitution of Propargylic Alcohols via o-Quinone Methide Intermediates: Brønsted Acid Catalyzed, Highly Enantio- and Diastereoselective Synthesis of 7-Alkynyl-12a-acetamido-Substituted Benzoxanthenes

2015 ◽  
Vol 17 (3) ◽  
pp. 648-651 ◽  
Author(s):  
Satyajit Saha ◽  
Christoph Schneider
Keyword(s):  
Nucleophilic Substitution ◽  
Quinone Methide ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diastereoselective Synthesis ◽  
Propargylic Alcohols ◽  
Brönsted Acid ◽  
Directing Group ◽  
Acid Catalyzed

Brønsted Acid-Catalyzed Nucleophilic Substitution of Alcohols

2006 ◽  
Vol 348 (14) ◽  
pp. 1841-1845 ◽  
Author(s):  
Roberto Sanz ◽  
Alberto Martínez ◽  
Delia Miguel ◽  
Julia M. Álvarez-Gutiérrez ◽  
Félix Rodríguez
Keyword(s):  
Nucleophilic Substitution ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed

Synthesis of 3-Allenylindoles and 3-Dienylindoles by Brønsted Acid Catalyzed Allenylation of 2-Arylindoles with Tertiary Propargylic Alcohols

Synlett ◽  
2009 ◽  
Vol 2009 (12) ◽  
pp. 1985-1989 ◽  
Author(s):  
Roberto Sanz ◽  
Mukut Gohain ◽  
Delia Miguel ◽  
Alberto Martínez ◽  
Félix Rodríguez
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Propargylic Alcohols ◽  
Brönsted Acid ◽  
Acid Catalyzed

Brønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitations

2010 ◽  
Vol 2010 (36) ◽  
pp. 7027-7039 ◽  
Author(s):  
Roberto Sanz ◽  
Delia Miguel ◽  
Alberto Martínez ◽  
Mukut Gohain ◽  
Patricia García-García ◽  
...  
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Propargylic Alcohols ◽  
Brönsted Acid ◽  
Acid Catalyzed

scholarly journals Brønsted acid-catalyzed hydroarylation of activated olefins

RSC Advances ◽  
2015 ◽  
Vol 5 (1) ◽  
pp. 493-496 ◽  
Author(s):  
Ivana Fleischer ◽  
Jola Pospech
Keyword(s):  
Quinone Methide ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Activated Olefins

A mild, regiospecific Brønsted acid-catalyzed hydroarylation of activated olefins, capable of the formation of quinone methide-like intermediates, has been investigated.

Brønsted Acid Catalyzed Dehydrative Nucleophilic Substitution of C3-Substituted 2-Indolylmethanols with Azlactones

Synthesis ◽  
2017 ◽  
Vol 50 (02) ◽  
pp. 295-302 ◽  
Author(s):  
Guang-Jian Mei ◽  
Feng Shi ◽  
Chen-Yu Bian ◽  
Dan Li ◽  
Qian Shi
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Direct Synthesis ◽  
Indole Derivatives ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Whole Process ◽  
Brönsted Acid ◽  
New Strategy ◽  
Acid Catalyzed

An efficient dehydrative nucleophilic substitution reaction of C3-substituted2-indolylmethanols with azlactones has been established. In the whole process, Brønsted acid was supposed to activate two substrates simultaneously. A series of structurally diversified indole derivatives were obtained in generally good yields and high diastereoselectivities (up to 86% yield, >95:5 dr). This protocol not only provides a new strategy for the direct synthesis of structurally diversified indole derivatives, but also enriches the chemistry of 2-indolylmethanols via dehydrative substitution reaction.

scholarly journals Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization

2018 ◽  
Vol 9 (37) ◽  
pp. 7327-7331 ◽  
Author(s):  
Keiji Mori ◽  
Nobuaki Umehara ◽  
Takahiko Akiyama
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diastereoselective Synthesis ◽  
Bond Functionalization ◽  
Hydride Shift ◽  
Brönsted Acid ◽  
Acid Catalyzed

Highly diastereoselective synthesis of tricyclic fused-pyrans was achieved by Brønsted acid catalyzed double C(sp3)–H bond functionalization.

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