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Stereoselective Synthesis



Stereoselective Synthesis

Robert S. Atkinson

ISBN: 978-0-471-95419-4 September 1995 542 Pages


Introduces a new, simplified classification for stereoselective reactions based on changes in the number of chiral centres taking place, emphasizing the three-dimensional representations of transition states in which stereoselectivity is determined. Using stereochemical vocabulary in accordance with IUPAC rules, it covers analysis of factors in which asymmetric induction occurs, the interplay between steric and electronic effects, the importance of conformational control, advantages of intramolecularity and the majority of important reaction types used in modern stereoselective synthesis.
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.