(Chemical Equation Presented) Ruthenium has twice the fun: The synthetic potential of the highly regio- and stereoselective title reaction, which relies on two oxidative cleavage steps promoted by RuCI3 in combination with NaIO 4 (see example; Bz = benzoyl), was demonstrated with the synthesis of biologically active cis-(2R,3S)-3-hydroxypipecolic acid from D-glucose. © 2010 Wiley-VCH Verlag GmbH &amp; Co. KGaA.

Sundarababu Baskaran

Department Of Chemistry

Ponminor Senthil Kumar

3-HYDROXYPIPECOLIC ACID

Benzylidene acetals

Chemical equations

D-glucose

HYDROXY CARBOXYLIC ACIDS

OXIDATIVE CLEAVAGES

Regio-selective

Stereo-selective

TERMINAL ALKENES

Carboxylic acids

glucose

Olefins

oxidation

Regioselectivity

ruthenium

Synthesis (chemical)

Organic acids

acetal derivative

alkene

benzylidene derivative

carboxylic acid

PERIODATE

PERIODIC ACID

article

chemistry

conformation

oxidation reduction reaction

Stereoisomerism

synthesis

X ray crystallography

Acetals

alkenes

Benzylidene Compounds

Crystallography, X-Ray

Molecular Conformation

Oxidation-Reduction

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Angewandte Chemie - International Edition

Stereoselective synthesis of 2-phenyl-oxazolines and 2-phenyl-oxazines via Lewis acid initiated intramolecular cyclization of benzylidene acetal with an azide functional group is described. © The Royal Society of Chemistry 2011.

Chemical Communications

A Lewis acid initiated intramolecular cyclization of benzylidene acetal with an azide functional group: Novel synthesis of oxazolines and oxazines

A stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid, starting from d-glucose is described. The key step in the overall synthesis is a highly regioselective reductive cleavage of benzylidene acetal 13 leading to hydroxymethyl piperidine derivative 14. © 2009 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

A regioselective reductive cleavage of benzylidene acetal: stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid

Phosphomolybdic acid supported on silica gel provides a truly catalytic method for the chemoselective cleavage of benzylidene acetals having sensitive functional groups under mild conditions. It is easy to perform on large scale owing to minimal catalyst loading (0.5 mol-%). Several sensitive functional groups such as TBDPS ether, -OMs, -OAc, allyl ether, N-Boc, N-Fmoc and N-Cbz are stable under the reaction conditions. In addition, benzylidene acetal is selectively cleaved in the presence of isopropylidene ketal. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

European Journal of Organic Chemistry

Truly catalytic and chemoselective cleavage of benzylidene acetal with phosphomolybdic acid supported on silica gel

A mild and efficient method for the regioselective oxidative cleavage of benzylidene acetals with KBrO3/Na2S2O4 under bi-phasic conditions (EtOAc/H2O), leading to highly functionalized chiral intermediates, is reported. © 2007.

Regioselective oxidative cleavage of benzylidene acetals: synthesis of highly functionalized chiral intermediates

Synthetically useful chiral intermediates have been synthesized starting from 1,3:4,6-di-O-benzylidene-D-mannitol by regioselective reductive cleavage using BF 3•Et 2O and Et 3SiH in high yields. © 2004 Elsevier Ltd. All rights reserved.

1,3:4,6-Di-O-benzylidene-D-mannitol as a source for novel chiral intermediates through regioselective reductive cleavage

Angewandte Chemie

10.1002/ange.v122.49

Regioselective oxidative cleavage of benzylidene acetals: Synthesis of α- and β-benzoyloxy carboxylic acids

Journal	Angewandte Chemie - International Edition
ISSN	14337851
Open Access	No