Diastereoselective Functionalization of Chiral N‐Acyl‐1,3‐oxazolidines and Their Applications in the Synthesis of Bioactive Molecules

1,3‐Oxazolidines, derived from widely available enantiomerically pure 1,2‐aminoalcohols, are versatile chiral auxiliaries for several key transformations, often serving as a platform for inquiries into new and complex reactivity. This Review focuses on the chemistry of N‐acyl‐1,3‐oxazolidines in whi...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-09, Vol.2022 (33), p.n/a
Main Authors: Morales‐Monarca, Gerardo H., Gnecco, Dino, Terán, Joel L.
Format: Article
Language:English
Subjects:
1,3-Oxazolidines
Asymmetric synthesis
Biological activity
Chemical synthesis
Chiral auxiliaries
Diastereoselectivity
Heterocycles
Natural products
Oxazolidine
Stereoselectivity
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Summary:1,3‐Oxazolidines, derived from widely available enantiomerically pure 1,2‐aminoalcohols, are versatile chiral auxiliaries for several key transformations, often serving as a platform for inquiries into new and complex reactivity. This Review focuses on the chemistry of N‐acyl‐1,3‐oxazolidines in which the stereoselective transformation is carried out on the N‐acyl attached side chain of the molecule, covering reports from late 1980s to 2020 across several fields of asymmetric synthesis of bioactive molecules, and in particular of natural products. 1,3‐Oxazoldine chiral auxiliaries are a valuable tool for asymmetric synthesis, often leading to the exploration of new chemistry, due to their ease of synthesis and functionalization. This Review summarizes the advances in the field, with a focus on the synthesis of bioactive molecules.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200267