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The semiempirical study on the addition of the chiral ammonium hypophosphite to an aldehyde

✍ Scribed by Jarosław Lewkowski

Book ID
102232242
Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
138 KB
Volume
15
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

The PM3 and AM1 semiempirical computations were performed in order to explain the stereochemistry of the addition of the chiral α‐methylbenzylammonium hypophosphite to an aldehyde, which is stereoselective to 100%. Both mechanisms: one considering the intermediate formation of α‐hydroxy phosphonous acids followed by the nucleophilic substitution with a chiral amine and the second considering the formation of a Schiff base followed by the addition of hypophosphorous acid to an azomethine bond were taken. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:162–168, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10230

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