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1,3-Phosphorotropic rearrangement of pyridyl phosphates to hydroxypyridyl phosphonates

✍ Scribed by Peter P. Onys'ko; Elena A. Suvalova; Tatiana I. Chudakova; Anatolii D. Sinitsa


Book ID
102227903
Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
298 KB
Volume
4
Category
Article
ISSN
1042-7163

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✦ Synopsis


Abstract

The lithium diisopropylamide (LDA) induced regioselective 1,3‐rearrangement of 3‐ and 2‐ pyridyl phosphates into the corresponding 3‐hydroxy‐4‐pyridyl‐and 2‐hydroxy‐3‐pyridylphosphonates has been observed and investigated. The rearrangement is proposed as a useful method for a directed introduction of a phosphoryl group into a hydroxypyridine nucleus.


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Benzyl dialkyl phosphates are deprotonated enantioselec-up to 50%. The pro-(S) hydrogen is removed by amides hatively by homochiral lithium amides of isopropyl( 1-phenyl-ving (S) configuration. Homochiral diethyl (S)-phenyl[D+ ethy1)amine or bis(1-phenylethy1)amine. The short-lived ben-methyl phosph