scispace - formally typeset
Search or ask a question
Journal ArticleDOI

Microwave Induced Ferrier Rearrangement

01 Aug 1994-Synthetic Communications (Taylor & Francis Group)-Vol. 24, Iss: 15, pp 2097-2101
TL;DR: In this paper, a short and facile entry to the 2, 3-unsaturated O-aryl glyco sides via microwave induced Ferrier rearrangement of acetylated glucal is reported.
About: This article is published in Synthetic Communications.The article was published on 1994-08-01. It has received 31 citations till now. The article focuses on the topics: Ferrier rearrangement & Glucal.
Citations
More filters
Journal ArticleDOI
TL;DR: Montmorillonite K10 was found to catalyze, under microwave irradiation, rapid O-glycosidation of 3,4,6-tri-O-acetyl-d-galactal to afford exclusively the alkyl and aryl 2,3-dideoxy-dthreo-hex-2-enopyranosides with very high α-selectivity as mentioned in this paper.

46 citations

Journal ArticleDOI
TL;DR: In this article, the structure and functionality of starch esters obtained in rotating roasters and in microwave ovens were examined and it was found that microwave heating is a convenient way to obtain a wide range of products of inorganic starch ester type usually produced in rotating Roasters.

44 citations

Journal ArticleDOI
TL;DR: A protocol that uses moist magnesium monoperoxyphthalate as an oxidant under microwave irradiation rapidly yields a variety of glycosyl sulfoxides from corresponding sulfides in high yields with high selectivity.
Abstract: A protocol that uses moist magnesium monoperoxyphthalate (MMPP) as an oxidant under microwave irradiation rapidly yields a variety of glycosyl sulfoxides from corresponding sulfides in high yields with high selectivity.

37 citations

Reference EntryDOI
TL;DR: Various elimination procedures conducted on appropriate pyranoid and furanoid carbohydrate derivatives, especially on O-protected glycosyl halides afford cyclic vinyl ethers which Fischer (inappropriately) named glycals, form the major part of this chapter.
Abstract: Various elimination procedures conducted on appropriate pyranoid and furanoid carbohydrate derivatives, especially on O-protected glycosyl halides afford cyclic vinyl ethers which Fischer (inappropriately) named glycals. These are used extensively in general organic synthesis and for the preparation of non-carbohydrate natural products as well as biologically important complex carbohydrates and glycoconjugates. The best known member, tri-O-acetyl-D-glucal, is normally made from tetra-O-acetyl-alpha-D-glucopyranosyl bromide, is commercially available, and is used very frequently in this chapter to represent the family in examples of the reactions under discussion. Because of the pronounced region- and stereoselectivities with which their addition reactions can be conducted, glycal derivatives are of major importance in synthesis. They also, however, take part in rearrangement processes that, likewise, have proved useful for synthesis. The principal one involves nucleophilic substitution of the allylic group with allylic rearrangement and results in products having double bonds in the 2, 3 positions and new substituents at the anomeric centers. By far the simplest and most commonly used way to this conversion involves the removal of the allylic substituent of the glycal and the generation of highly resonance-stabilized oxocarbenium ion intermediate. This may then react with nucleophiles at the anomeric center to give products as mixtures of diastereomers. Many examples and variations of this theme are described and form the major part of this chapter, but other ways are also considered Almost no formal mechanistic studies have been carried out on the reactions in this chapter. Categorization of mechanism required for the treatment of this topic has been done on the basis of conditions used, product identification and largely, chemical intuition. Keywords: glycals; transformation; oxocarbenium ions; regioselectivity; diasterioselectivity; nucleophilic substitutions; homoallylic center; addition-elimination reactions; palladium; leaving groups; electrocyclic reactions; unsaturated compounds; free sugars; glycosyl peroxides; glycosyl caroxylates; S-glycosides; glycosyl halides; glycosyl azides; glycosyl phosphonates; glycosyl hydrides; furanoid glycols; intramolecular applications; reverse reaction; reaction variations; scope; limitations; configuration; experimental procedures; other methods

36 citations

Journal ArticleDOI
TL;DR: Microwave irradiation of a mixture of tri-O -acetyl-d -glucal 1 and an appropriate alcohol 2a-f, in the presence of Montmorillonite K-10 as a catalyst, provided unsaturated glycosides 3a- f in much shorter time and in yields comparable with conventional heating.

32 citations

References
More filters
Journal ArticleDOI
TL;DR: In this paper, four different types of organic reactions have been studied and seven different organic compounds have been prepared, under pressure in a microwave oven, and considerable rate increases have been observed.

1,509 citations

Journal ArticleDOI
TL;DR: In this article, commercial microwave ovens have been safely used to dramatically reduce the reaction times (at comparable yield) of Diels-Alder, Claisen, and ene reactions.

1,028 citations

Journal ArticleDOI
TL;DR: In this paper, the authors present a review of applications of microwave energy in ORGANIC CHEMISTRY, focusing on the application of MICROWAVE ENERGY in organic preparation and procedures.

380 citations