Literature DB >> 15770618

"Designer acids": combined acid catalysis for asymmetric synthesis.

Hisashi Yamamoto1, Kentaro Futatsugi.   

Abstract

Lewis and Brønsted acids can be utilized as more-effective tools for chemical reactions by sophisticated engineering ("designer acids"). The ultimate goal of such "designer acids" is to form a combination of acids with higher reactivity, selectivity, and versatility than the individual acid catalysts. One possible way to take advantage of such abilities may be to apply a "combined acids system" to the catalyst design. The concept of combined acids, which can be classified into Brønsted acid assisted Lewis acid (BLA), Lewis acid assisted Lewis acid (LLA), Lewis acid assisted Brønsted acid (LBA), and Brønsted acid assisted Brønsted acid (BBA), can be a particularly useful tool for the design of asymmetric catalysis, because combining such acids will bring out their inherent reactivity by associative interaction, and also provide more-organized structures that allow an effective asymmetric environment.

Entities:  

Year:  2005        PMID: 15770618     DOI: 10.1002/anie.200460394

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  41 in total

1.  Enantioselective addition of boronates to chromene acetals catalyzed by a chiral Brønsted acid/Lewis acid system.

Authors:  Philip N Moquist; Tomohiro Kodama; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-17       Impact factor: 15.336

2.  Enantioselective boronate additions to N-acyl quinoliniums catalyzed by tartaric acid.

Authors:  Tomohiro Kodama; Philip N Moquist; Scott E Schaus
Journal:  Org Lett       Date:  2011-11-08       Impact factor: 6.005

3.  Enantioselective synthesis of pyrroloindolines by a formal [3 + 2] cycloaddition reaction.

Authors:  Lindsay M Repka; Jane Ni; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

4.  Enantioselective route to platensimycin: an intramolecular Robinson annulation approach.

Authors:  Pingfan Li; Joshua N Payette; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2007-07-14       Impact factor: 15.419

Review 5.  Recent advances in the chemistry and biology of naturally occurring antibiotics.

Authors:  K C Nicolaou; Jason S Chen; David J Edmonds; Anthony A Estrada
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones.

Authors:  Cheol Hong Cheon; Osamu Kanno; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

7.  Synthesis and biological evaluation of ABCD ring fragments of the kibdelones.

Authors:  David L Sloman; Branko Mitasev; Stephen S Scully; John A Beutler; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-18       Impact factor: 15.336

8.  Metal-free Regioselective Hydrochlorination of Unactivated Alkenes via a Combined Acid Catalytic System.

Authors:  Shengzong Liang; Gerald B Hammond; Bo Xu
Journal:  Green Chem       Date:  2018-01-02       Impact factor: 10.182

9.  Cationic-oxazaborolidine-catalyzed enantioselective Diels-Alder reaction of alpha,beta-unsaturated acetylenic ketones.

Authors:  Joshua N Payette; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.

Authors:  Jessica Z Chan; Ahmet Yesilcimen; Min Cao; Yuyang Zhang; Bochao Zhang; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419

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