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.

Satyanarayana Raja Bhushan Reddy

carbonic acid

ether

furan derivative

iodide

addition reaction

Alkylation

article

Michael addition

stereochemistry

substitution reaction

synthesis

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

Tetrahedron Letters

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

Tandem radical cyclization to vinylogous carbonates and carbamates is developed for a new, highly stereoselective synthesis of heterocyclic angular triquinanes. The strategy is also useful to gain access to oxa- and azatriquinanes, which incorporate the spiroindoline moiety. The method is further extended to the synthesis of lactone-bearing as well as uracil-fused angular triquinanes. © 2012 American Chemical Society.

Organic Letters

Stereoselective synthesis of oxa- and aza-angular triquinanes using tandem radical cyclization to vinylogous carbonates and carbamates

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.

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

An efficient strategy is developed for the synthesis of 1,2,2-trisubstituted indane derivatives employing a tandem SN2- Michael reaction sequence. The method is extended towards the synthesis of spiroindanes and indanopiperidines. © Georg Thieme Verlag Stuttgart.

Synlett

Stereoselective synthesis of 1,2,2-trisubstituted indane derivatives using a tandem SN2-michael addition sequence

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

Cambridge Crystallographic Data Centre (CCDC)

Journal of English for Academic Purposes

Ch-Ch-Ch-Ch changes

An efficient strategy is developed for the stereoselective synthesis of unsymmetrical dioxa-cage compounds containing ether linkages employing a 6-exo-trig alkyl radical cyclization to vinylogous carbonates. The radical precursors are obtained from the Diels-Alder adducts via iodoetherification and conversion of the alcohol moiety to vinylogous carbonate. The formation of mono-oxa-cage compounds via an intramolecular 5-exo-trig alkyl radical cyclization to olefin is also described. © Georg Thieme Verlag Stuttgart.

Journal	Tetrahedron Letters
ISSN	00404039
Open Access	No