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Título del libro: Imides: Medicinal, Agricultural, Synthetic Applications And Natural Products Chemistry
Título del capítulo: Chiral sulfur-containing imide auxiliaries in medicinal chemistry

Autores UNAM:
ROSMARBEL MORALES NAVA;
Autores externos:

Idioma:

Año de publicación:
2019
Palabras clave:

Acetate aldol; Aldol; Glycolate aldol; Michael addition; Oxazolidinethione; Thiazolidinethione


Resumen:

This chapter reviews the synthetic applications and recent advances of chiral 1,3-thiazolidine-2-thione and 1,3-oxazolidine-2-thione auxiliaries in the last two decades. It reviews the preparation of these chiral auxiliaries from chiral aminoacids, coupling of acyl groups to the auxiliaries, acyl aldol reactions, and particularly the acetate aldol reaction, glycolate aldol reactions, titanium enolate additions to dialkyl acetals, titanium enolate additions to glycals, intramolecular rearrangement of sulfur in N-enoyl derivatives, Michael additions to N-enoyl derivatives, titanium enolate addition to aldimines, sodium enolate addition/elimination to ß-iodoacrylates, and resolution of racemic mixtures. Also, it includes cleavage methods commonly used in syntheses. Most of these methodologies have found application in the syntheses of a variety of natural products with different degrees of complexity. © 2019 Elsevier Inc. All rights reserved.


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