Advances In Free Radical Chemistry, Volume 2, Volume 2 (advances In Free Radical Chemistry)

ADVANCES IN FREE RADICAL CHEMISTRY Volume 2 • 1999 This Page Intentionally Left Blank ADVANCES IN FREE RADICAL CHEMISTRY Editor: SAMIRZ.ZARD Departement de Synthese Organ ique Ecole Polytechnique Palaiseau, France VOLUME 2 • 1999 (iSi)JAI PRESS INC. V _ ^ Stamford, Connecticut Copyright © 1999 JAI PRESS INC 100 Prospea Street Stamford, Connecticut 06904-0811 All rights reserved. No part of this publication may be reproduced, stored on a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, filming, recording, or otherwise, without prior permission in writing from the publisher. ISBN: 1-55938-321-6 Transferred to digital printing 2006 CONTENTS LIST OF CONTRIBUTORS vii PREFACE SamirZ.Zard ix RADICAL INTERMEDIATES IN THE REACTION OF LYSINE 2,3-AMINOMUTASE Perry A. Frey and Squire Booker 1 GENERATION OF RADICAL SPECIES BY SINGLE-ELECTRON-TRANSFER REACTIONS AND THEIR APPLICATION TO THE DEVELOPMENT OF SYNTHETIC REACTIONS Tetsuhiro Mikami and Koichi Narasaka 45 RADICAL INTERMEDIATES IN THE STEREOSELECTIVE SYNTHESIS OF C-GLYCOSIDES Troels Skrydstrup and Jean-Marie Beau 89 REACTIONS OF ARENEDIAZONIUM SALTS WITH TETRATHIAFULVALENE AND RELATED ELECTRON DONORS: A STUDY OF "RADICAL-POLAR CROSSOVER" REACTIONS Nadeem Bashir, Balaram Patro, and John A. Murphy RADICAL CYCLIZATION OF N-AZIRIDINYLIMINES: ITS APPLICATION TO SESQUITERPENE SYNTHESES VIA CONSECUTIVE CARBON-CARBON BOND FORMATION APPROACH Sunggak Kim INDEX 123 151 203 This Page Intentionally Left Blank LIST OF CONTRIBUTORS Nadeem Bashir Department of Pure and Applied Chemistry University of Strathclyde Glasgow, Scotland Jean-Marie Beau Laboratoire de Synthase de Biomol^cules University Paris-Sud Paris, France Squire Booker Department of Biochemistry University of Wisconsin-Madison Madison, Wisconsin Perry A. Frey Department of Biochemistry University of Wisconsin-Madison Madison, Wisconsin Sunggak Kim Tetsuhiro Mikami Department of Chemistry Korea Advanced Institute of Science and Technology Taejon, Korea Department of Chemistry The University of Tokyo Tokyo, Japan John A. Murphy Department of Pure and Applied Chemistry University of Strathclyde Glasgow, Scotland Kiochi Narasaka Department of Chemistry The University of Tokyo Tokyo,Japan VII viii Balaram Patro LIST OF CONTRIBUTORS Department of Pure and Applied Chemistry University of Strathclyde Glasgow, Scotland Troels Skrydstrup Department of Chemistry Aarhus University Aarhus C, Denmark PREFACE The impact of free radical chemistry over the past two decades on the fields of organic synthesis and biochemistry has been enormous. Hardly a total synthesis is now published not involving one or more radical steps, be it a Barton-McCombie deoxygenation or a tin hydride-mediated carbon-carbon bond-forming cascade. Recent years have also seen the emergence of highly useful redox systems based on transition metals, such as manganese or samarium, or exploiting electron transfer from nonmetallic entities such as phenolates or tetrathiafulvenes. In parallel to the development of new radical processes, much effort has been invested in the study and understanding of radical transformations at a more fundamental leve