361 Topics in Current Chemistry

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1 361 Topics in Current Chemistry Editorial Board: H. Bayley, Oxford, UK K.N. Houk, Los Angeles, CA, USA G. Hughes, CA, USA C.A. Hunter, Sheffield, UK K. Ishihara, Chikusa, Japan M.J. Krische, Austin, TX, USA J.-M. Lehn, Strasbourg Cedex, France R. Luque, C ordoba, Spain M. Olivucci, Siena, Italy J.S. Siegel, Nankai District, China J. Thiem, Hamburg, Germany M. Venturi, Bologna, Italy C.-H. Wong, Taipei, Taiwan H.N.C. Wong, Shatin, Hong Kong

2 Aims and Scope The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage includes all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether at the university or in industry, a comprehensive overview of an area where new insights are emerging that are of interest to larger scientific audience. Thus each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years should be presented. A description of the laboratory procedures involved is often useful to the reader. The coverage should not be exhaustive in data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Discussion of possible future research directions in the area is welcome. Review articles for the individual volumes are invited by the volume editors. Readership: research chemists at universities or in industry, graduate students. More information about this series at

3 Jean-Luc Montchamp Editor Phosphorus Chemistry II Synthetic Methods With contributions by I. Abdellah C. Alayrac A.-C. Gaumont P.R. Hanson S. Jayasinghe A. Kraszewski S. Lakhdar S. Maitra R.K. Malla J.L. Markley J.-L. Montchamp M. Sobkowski C.D. Spilling J. Stawinski

4 Editor Jean-Luc Montchamp Department of Chemistry Texas Christian University Fort Worth, Texas USA ISSN ISSN (electronic) Topics in Current Chemistry ISBN ISBN (ebook) DOI / Library of Congress Control Number: Springer Cham Heidelberg New York Dordrecht London Springer International Publishing Switzerland 2015 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made. Printed on acid-free paper Springer International Publishing AG Switzerland is part of Springer Science+Business Media (

5 Preface The element phosphorus was discovered early in the seventeenth century, as chronicled in John Emsley s excellent and fascinating book The 13th Element. Phosphorus chemistry is often perceived as an old Dame in the chemical arts. This is because many important reactions were discovered at the turn of the twentieth century, largely from the contributions of Russian chemists. Since then, phosphorus chemistry has unfortunately been considered a mature and specialized field. However, phosphorus being key to all life processes, tremendous opportunities for phosphorus research have remained ever since. So the old Dame is now experiencing a second (or third?) youth. It has been my privilege to guest-edit these two volumes for Topics in Current Chemistry on phosphorus chemistry, and I am grateful to Mike Krische who gave me this opportunity. Topics in Current Chemistry has already produced several excellent volumes on various aspects of phosphorus chemistry. The present volumes are dedicated to various topics in organophosphorus chemistry. The first volume concerns biologically-related topics (phosphinopeptides, phosphinic acids, prodrugs) as well as P-asymmetric compounds (also called P-stereogenic, P-chiral, etc. there is still some intense discussion about how to name this field!). The second volume deals with various synthetic methods and phosphorus functionalities (P-BH 3, phospho-aldol, H- and C-phosphonates, phosphorus tethers in synthesis, and C H to C P transformations). In some cases, prior reviews were available on some of the topics. However, the present chapters constitute the best, most up-to-date and in-depth resource in the field, which has been growing rapidly in the past 5 10 years. I believe these volumes will be important additions to library shelves, both institutional and personal. The writings are appropriate for experts and interested students alike. These chapters have been written by internationally recognized leading experts in the field, both European and American researchers having contributed to the volumes. I wish to thank personally all these authors for spending countless hours to produce these outstanding chapters, which are important contributions to the chemical literature. Clearly, phosphorus chemistry is not only alive and well, but v

6 vi Preface has a promising future and offers great potential for scientific discoveries. Too often people assume that a well-researched topic no longer has anything to offer. I think these chapters prove that nothing could be further from the truth. Because phosphorus is such an important element, chemical research in organophosphorus chemistry has a very bright future indeed. The old Dame will remain young! Fort Worth, TX, USA 9 November 2014 Jean-Luc Montchamp

7 Contents Recent Advances in Synthesis of P-BH 3 Compounds... 1 Carole Alayrac, Sami Lakhdar, Ibrahim Abdellah, and Annie-Claude Gaumont Synthesis of Non-racemic α-hydroxyphosphonates via Asymmetric Phospho Aldol Reaction Christopher D. Spilling and Raj K. Malla Recent Advances in H-Phosphonate Chemistry. Part 1. H-Phosphonate Esters: Synthesis and Basic Reactions Michal Sobkowski, Adam Kraszewski, and Jacek Stawinski Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives Michal Sobkowski, Adam Kraszewski, and Jacek Stawinski Carbon Hydrogen to Carbon Phosphorus Transformations Jean-Luc Montchamp Phosphate Tethers in Natural Product Synthesis Paul R. Hanson, Susanthi Jayasinghe, Soma Maitra, and Jana L. Markley Index vii