Literature DB >> 19175350

Asymmetric bisboranes as bidentate catalysts for carbonyl substrates.

Andrew A Rodriguez1, Carrie Zhao, Kenneth J Shea.   

Abstract

A new class of C(2) symmetric bisoxazaborolidinone compounds is described which exhibits bidentate binding to carbonyl substrates. Using the Diels-Alder reaction as a model system, the catalytic activity of these bis-Lewis acids is probed. Reaction rates and selectivities are observed that are higher than the corresponding mono-Lewis acids. This novel system offers a potentially powerful new approach to asymmetric Lewis acid catalysis.

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Year:  2009        PMID： 19175350      PMCID： PMC2662717          DOI： 10.1021/ol802793k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Binuclear Metallohydrolases.

Authors:  Dean E. Wilcox
Journal:  Chem Rev       Date:  1996-11-07       Impact factor: 60.622

Review 2.  The catalytic mechanisms of binuclear metallohydrolases.

Authors:  Natasa Mitić; Sarah J Smith; Ademir Neves; Luke W Guddat; Lawrence R Gahan; Gerhard Schenk
Journal:  Chem Rev       Date:  2006-08       Impact factor: 60.622

3.  Intramolecular Diels-Alder reactions of ester-tethered 1,7,9-decatrienoates: bis[chloro(methyl)aluminum]trifluoromethanesulfonamide as a catalyst.

Authors:  Akio Saito; Hisanaka Ito; Takeo Taguchi
Journal:  Org Lett       Date:  2002-12-26       Impact factor: 6.005

4.  Oxazaborolidine-derived Lewis acid assisted Lewis acid as a moisture-tolerant catalyst for enantioselective Diels-Alder reactions.

Authors:  Kentaro Futatsugi; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-25       Impact factor: 15.336

5.  The first general enantioselective catalytic Diels-Alder reaction with simple alpha,beta-unsaturated ketones.

Authors:  Alan B Northrup; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

6.  Asymmetric 1,3-dipolar cycloadditions of nitrones and methacrolein catalyzed by chiral bis-titanium lewis acid: a dramatic effect of N-substituent on nitrone.

Authors:  Takuya Hashimoto; Masato Omote; Taichi Kano; Keiji Maruoka
Journal:  Org Lett       Date:  2007-10-11       Impact factor: 6.005

7.  Asymmetric Lewis acid-catalyzed Diels-Alder reactions of alpha,beta-unsaturated ketones and alpha,beta-unsaturated acid chlorides.

Authors:  Joel M Hawkins; Mitch Nambu; Stefan Loren
Journal:  Org Lett       Date:  2003-11-13       Impact factor: 6.005

8.  (2,7-Disubstituted-1,8-biphenylenedioxy)bis(dimethylaluminum) as bidentate organoaluminum Lewis acids: elucidation and synthetic Utility of the double electrophilic activation phenomenon.

Authors:  Takashi Ooi; Makoto Takahashi; Masao Yamada; Eiji Tayama; Kiyoyuki Omoto; Keiji Maruoka
Journal:  J Am Chem Soc       Date:  2004-02-04       Impact factor: 15.419

9.  Broad-spectrum enantioselective diels-alder catalysis by chiral, cationic oxazaborolidines.

Authors:  Do Hyun Ryu; Thomas W Lee; E J Corey
Journal:  J Am Chem Soc       Date:  2002-08-28       Impact factor: 15.419

10.  Oxazaborolidinone-catalyzed enantioselective Diels-Alder reaction of acyclic alpha,beta-unsaturated ketones.

Authors:  Ram Shanker Singh; Shinya Adachi; Fumi Tanaka; Toyonao Yamauchi; Chieko Inui; Toshiro Harada
Journal:  J Org Chem       Date:  2007-12-06       Impact factor: 4.354
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