Directed Selectivity in Organic Synthesis

[Book Description]

Bringing together examples that until now were often hidden and widely spread throughout the original literature, this textbook shows how to use the correct reagents, conditions or reaction sequences to have access to all possible stereoisomers when beginning synthesis with only a single starting material. Adopting a didactic approach, the authors have chosen general and simple examples throughout the book so that these reactions can be transferred easily to other reaction types. While of major interest to master and PhD students alike, this book is also a source of valuable information for organic chemists in both academia and industry.

[Table of Contents]

Preface VII Acknowledgement                        IX
1 General Methods to Direct Selectivity            1  (64)
  1.1 Chemoselectivity                             1  (6)
  1.2 Regioselectivity                             7  (19)
  1.3 Stereoselectivity                            26 (22)
  1.4 Enatioselectivity                            48 (12)
  References                                       60 (5)
2 Directed Selectivity: Acetylenes and Alkenes     65 (76)
  2.1 Acetylenes                                   65 (9)
  2.2 Alkenes                                      74 (61)
    2.2.1 Hydrogenation and Reduction              74 (7)
    2.2.2 Hydroformylation                         81 (3)
    2.2.3 Oxidation and Allyl Oxidation            84 (5)
    2.2.4 Allyl Substitution                       89 (21)
    2.2.5 Cycloaddition                            110(10)
    2.2.6 Sigmatropic Rearrangement                120(5)
    2.2.7 Ene Reaction                             125(3)
    2.2.8 Heck Cyclization                         128(2)
    2.2.9 Pauson-Khand Reaction                    130(1)
    2.2.10 Metathesis Cyclization                  131(2)
    2.2.11 Radical and Nucleophilic Cyclization    133(2)
  References                                       135(6)
3 Directed Selectivity with Carbonyl Derivatives   141(76)
  3.1 Carbonyl Compounds as Electrophiles          141(37)
    3.1.1 1,2-Addition of Nucleophiles to          141(10)
    Carbonyls
    3.1.2 Reduction of Carbonyl Compounds          151(12)
    3.1.3 Allylation/Crotylation Reactions         163(15)
  3.2 Conjugate Addition to Carbonyl Compounds     178(7)
    3.2.1 Cuprate Additions                        178(3)
    3.2.2 Enolate Additions                        181(1)
    3.2.3 Free Radical Addition to Enoates         182(2)
    3.2.4 Olefin Formation by Organometal          184(1)
    Addition to Alkynes
  3.3 Enolate Derivatives                          185(9)
  3.4 Miscellaneous                                194(14)
    3.4.1 Rearrangements and Fragmentations        194(4)
    3.4.2 Pericyclic Reactions                     198(2)
    3.4.3 Lewis Acid-Mediated Carbonyl ene         200(1)
    Reactions
    3.4.4 Organometal-Mediated C-C Connections     201(1)
    3.4.5 Metal Complex Formation in Carbonyl      202(3)
    and Imine Additions
    3.4.6 Wittig-Type Reactions                    205(2)
    3.4.7 Oxidation Reactions                      207(1)
  References                                       208(9)
4 Selectivity at spｳ-Centers and Heteroatoms       217(128)
  4.1 Epoxides                                     217(32)
  4.2 Acetals                                      249(17)
  4.3 Ethers                                       266(19)
  4.4 Alcohols and Phenols                         285(18)
  4.5 Sulfur Compounds                             303(15)
  4.6 Amines                                       318(16)
  4.7 Halogen Compounds                            334(11)
References                                         345(10)
Index                                              355