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.

Sundarababu Baskaran

Department Of Chemistry

Ponminor Senthil Kumar

2 PHENYL OXAZINE DERIVATIVE

2 PHENYL OXAZOLINE DERIVATIVE

Azide

benzylidene derivative

Lewis acid

oxazine derivative

oxazoline derivative

unclassified drug

article

Cyclization

stereochemistry

synthesis

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IIT Madras

Chemical Communications

A diversity-oriented synthesis is described for functionalized chiral building blocks (i.e., 7, 9, 10, 16, and 17) and the biologically active iminosugar, fucosidase inhibitor (2S,3R,4R,5R)-2-(hydroxymethyl)-5- methylpyrrolidine-3,4-diol (22), starting from common chiral intermediate 1a which is obtained through a regioselective reductive cleavage of a bis(benzylidene) acetal. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

European Journal of Organic Chemistry

Diversity-oriented synthesis of useful chiral building blocks from D-mannitol

(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.

Angewandte Chemie - International Edition

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

Journal	Data powered by TypesetChemical Communications
Publisher	Data powered by TypesetRoyal Society of Chemistry
ISSN	13597345
Open Access	No