A stereoselective method for the synthesis of substituted tetrahydropyran derivatives employing a tandem SN2-Michael addition sequence to vinylogous carbonates is developed. The method is extended to the synthesis of bicyclic ether motifs present in polyether ladder toxins. © 2009 American Chemical Society.

Satyanarayana Raja Bhushan Reddy

ether derivative

pyran derivative

vinyl derivative

Alkylation

article

chemical structure

chemistry

Stereoisomerism

synthesis

X ray crystallography

Crystallography, X-Ray

Ethers, Cyclic

Models, Molecular

Pyrans

Vinyl Compounds

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

Organic Letters

An intramolecular, benzylic C(sp3)-C(sp2) bond forming Heck reaction on vinylogous carbonates (or β-alkoxyacrylates) is developed for an efficient synthesis of isochromene derivatives. A competitive Heck reaction between a normal olefin and a vinylogous carbonate moiety led to a dihydronaphthalene product via coupling with olefin exclusively. The method was used in the synthesis of a core of cis-dihydrokalafungin and monocerolide. © the Partner Organisations 2014.

RSC Advances

Synthesis of isochromene derivatives using an intramolecular benzylic C(sp3)-C(sp2) bond forming Heck reaction on vinylogous carbonates

A tandem SN2 alkylation/Michael addition to vinylogous carbonates based approach for the stereoselective synthesis of benzoxepines is developed. The stereoselectivity improves with an increase in the steric bulk of the substituents. The method is extended to the synthesis of benzopyranoxepines and benzoxepinopyridines with angular substituents. A tandem SN2 alkylation/Michael addition to vinylogous carbonates based approach for the stereoselective synthesis of benzoxepines is developed. The stereoselectivity improves with an increase in the steric bulk of the substituents. The method is extended to the synthesis of benzopyranoxepines and benzoxepinopyridines with angular substituents. Copyright © 2013 WILEY-VCH Verlag GmbH &amp; Co. KGaA, Weinheim.

European Journal of Organic Chemistry

Stereoselective synthesis of benzoxepines through tandem alkylation/Michael addition to vinylogous carbonates

A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbamates with carbenes in the presence of Cu(acac) 2 as the catalyst has been developed for the construction of cyclopropapyrrolidinones. The 'syn' isomer of N-DAC can be converted to the 'anti' isomer by simple silica gel treatment. Regioselective cleavage of each of the cyclopropane bonds of these two acceptor substituted N-DACs led to a diverse array of azacycles. © 2012 The Royal Society of Chemistry.

Organic and Biomolecular Chemistry

Stereoselective synthesis and applications of nitrogen substituted donor-acceptor cyclopropanes (N-DACs) in the divergent synthesis of azacycles

A stereoselective method for the synthesis of substituted tetrahydrofuran derivatives employing a tandem alkylation-Michael addition sequence to vinylogous carbonates is developed. The method could be used to synthesize THFs bearing tertiary ethers. Further, the method is extended to the synthesis of adjacent bis-THFs. © 2010 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

Tandem SN2-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,5-tetrasubstituted tetrahydrofurans

An intramolecular, alkyne iminium ion cyclization of vinylogous carbamates derived from o-alkynyl anilines and N-protected homopropargyl amines is developed for the stereoselective construction of trans-2,3-disubstituted indolines and pyrrolidine derivatives, respectively. The regioselectivity of the alkyne iminium ion cyclization could be switched using a hydroxy group as an internal nucleophile resulting in cyclic ether-fused 1,2-dihydroquinolines. The entire process of nitrogen heterocycle formation can also be carried out in a 'one-pot' manner starting from o-iodo aniline derivatives. © The Royal Society of Chemistry.

Chemical Communications

Stereoselective synthesis of 2,3-disubstituted indoline, pyrrolidine and cyclic ether-fused 1,2-dihydroquinoline derivatives using alkyne iminium ion cyclization of vinylogous carbamates: Switch of regioselectivity using an internal hydroxy group as a nucleophile

Efficient Stereochemical Relay en Route to Leucascandrolide A

Tandem alkylation - Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,6-tetrasubstituted tetrahydropyrans

Journal	Organic Letters
ISSN	15237060
Open Access	No