Enantiomeric Impurities in Chiral Catalysts, Auxiliaries, Synthons and Resolving Agents. Part 2

Abstract

The enantiomeric purity of reagents used in asymmetric synthesis is of fundamental importance when evaluating the selectivity of a reaction and the product purity. In this work, 109 chiral reagents (many recently introduced) are assayed. Approximately 64% of these reagents had moderate to high levels of enantiomeric impurities (i.e. from > 0.1% to < 16%). The type of chiral reagents assayed and used in enantioselective synthesis. Include: (a) metal- ligand catalysts for allylic substitutions, catalysts for addition of Grignard reagents and other additions, epoxidations and reduction of ketones and aldehydes; (b) Ru-complex auxiliaries for asymmetric cyclopropanation, as well as amine, diamine, alcohol, diol, aminoalcohol, carboxylic acid and oxazolidione auxiliaries; (c) epoxide, lactone, furanone, pyrrolidinone, nitrile, sulfoximine and carboxylic acid synthons (including malic acid, mandelic acid, lactic acid and tartaric acid); and (d) a variety of chiral resolving agents. Accurate, efficient assays for all compounds are given.

Department(s)

Chemistry

Comments

National Institutes of Health, Grant GM53825-03

International Standard Serial Number (ISSN)

0957-4166

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2024 Elsevier, All rights reserved.

Publication Date

15 Jan 1999

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