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Stereoselective Synthesis

  • ID: 2176089
  • Book
  • 542 Pages
  • John Wiley and Sons Ltd
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Stereoselective Synthesis considers the methods available for the synthesis of simple target molecules, the majority containing not more than two chiral centres, as single stereoisomers. This volume focuses on the factors which give rise to the stereoselectivity and classifies stereoselective reactions accordingly. This classification, and the extensive use of 3–D representations, enables the student to understand the stereochemistry of these reactions and hence apply them to the synthesis of previously unseen target molecules as single stereoisomers. Stereoselective Synthesis presents:

∗ a new, unique, simplified classification for stereoselective reactions based on the number of chiral centres created in the product by comparison with the number present in the starting material

∗ coverage of the majority of important reaction types used in modern stereoselective synthesis

∗ a detailed analysis of factors which bring about asymmetric induction: the interplay between steric and electronic effects, the importance of conformational control and the advantages of intramolecularity in reactions

∗ emphasis on synthesis of simple target molecules and on those steps which involve stereochemistry

∗ realistic 3–D representations of transition states in which stereoselectivity is created

∗ stereochemical vocabulary in accordance with IUPAC rules

Stereoselective Synthesis is an invaluable aid not only to students in understanding this important area but also to those actively engaged in the syntheses of target molecules as single stereoisomers.
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Partial table of contents:

Type 0 Reactions: Reactions in Which No New Chiral Centres Are Created.

Type I Reactions: Those Proceeding with Either Inversion or with Retention of Configuration at a Single Chiral Centre.

Simple Chirality Transfer Reactions: Those in Which a Single Chiral Centre Is Transferred with Concomitant Migration of One or More Double Bonds.

Type II Reactions: Simple Diastereoselectivity in 1,2–Additions to Alkenes, Diels–Alder and 1,3–Dipolar Cycloadditions and the ene Reaction.

Type II Reactions: Occasional Diastereoselectivity.

Type III Reactions: Those Involving Asymmetric Induction.

Type III Reactions of Diastereotopic and Enantiotopic Atoms and Groups;

Enzyme Catalysed Reactions.

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Robert S. Atkinson
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