(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol:  Chiral Auxiliary and Efficient Protecting Group for Boronic Acids

2000 ◽  
Vol 65 (26) ◽  
pp. 9194-9200 ◽  
Author(s):  
Joachim E. A. Luithle ◽  
Jörg Pietruszka
Keyword(s):  
Boronic Acids ◽  
Chiral Auxiliary ◽  
Protecting Group

A Chiral Benzyl Group as a Chiral Auxiliary and Protecting Group for the Synthesis of Optically Active 1,2-Diols and (+)-Frontalin

Synlett ◽  
2013 ◽  
Vol 25 (02) ◽  
pp. 251-254 ◽  
Author(s):  
Hee-Doo Kim ◽  
Tae Kim ◽  
Young-Kyo Kim ◽  
Zunhua Yang ◽  
Jung Jung ◽  
...  
Keyword(s):  
Optically Active ◽  
Chiral Auxiliary ◽  
Protecting Group

(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates

2012 ◽  
Vol 84 (11) ◽  
pp. 2339-2416 ◽  
Author(s):  
C. Annette Berg ◽  
Nils C. Eichenauer ◽  
Jörg Pietruszka
Keyword(s):  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Boronic Acids ◽  
Protecting Group ◽  
Enantiomerically Pure

Tartrate-derived (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol has found diverse applications in asymmetric organic synthesis. Among these, its utilization as a protecting group for boronic acids has been investigated extensively. Besides being extraordinarily stable and thus allowing a plethora of transformations, it enables access to various diastereo- and enantiomerically pure organoboron reagents and versatile intermediates in asymmetric synthesis.

A novel redox-sensitive protecting group for boronic acids, MPMP-diol

2005 ◽  
Vol 46 (49) ◽  
pp. 8503-8505 ◽  
Author(s):  
Jun Yan ◽  
Shan Jin ◽  
Binghe Wang
Keyword(s):  
Boronic Acids ◽  
Protecting Group

A Novel Redox-Sensitive Protecting Group for Boronic Acids, MPMP-Diol.

ChemInform ◽  
2006 ◽  
Vol 37 (12) ◽  
Author(s):  
Jun Yan ◽  
Shan Jin ◽  
Binghe Wang
Keyword(s):  
Boronic Acids ◽  
Protecting Group

scholarly journals meta-Selective C–H functionalisation of aryl boronic acids directed by a MIDA-derived boronate ester

2020 ◽  
Vol 11 (12) ◽  
pp. 3301-3306 ◽  
Author(s):  
Alexander F. Williams ◽  
Andrew J. P. White ◽  
Alan C. Spivey ◽  
Christopher J. Cordier
Keyword(s):  
Acid Derivative ◽  
Boronic Acids ◽  
Protecting Group ◽  
Boronate Ester ◽  
Methyliminodiacetic Acid

An N-methyliminodiacetic acid derivative allows the meta-C–H functionalisation of boronic acids, acting simultaneously as a directing and protecting group.

A Mild and Simple Method for Making MIDA Boronates

2020 ◽  
Author(s):  
Aidan Kelly ◽  
Peng-Jui (Ruby) Chen ◽  
Jenna Klubnick ◽  
Daniel J. Blair ◽  
Martin D. Burke
Keyword(s):  
Organic Synthesis ◽  
Boronic Acids ◽  
Simple Method ◽  
Direct Preparation ◽  
Synthesis Procedure ◽  
Harsh Conditions

<div> <div> <div> <p>Existing methods for making MIDA boronates require harsh conditions and complex procedures to achieve dehydration. Here we disclose that a pre-dried form of MIDA, MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in labs that do not specialize in organic synthesis. </p> </div> </div> </div>

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