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Asymmetric Mannich-Type Synthesis of N-Phosphinyl α-Aminophosphonic Acid Monoesters

✍ Scribed by Zhijia Fang; Haohao Yang; Zhiwei Miao; Ruyu Chen

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
198 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A convenient diastereoselective synthesis of diisopropyl (2__R__,3__R__)‐3‐{{{(R/S)‐aryl[(diethoxyphosphinyl)amino]methyl}hydroxyphosphinyl}oxy}‐2‐hydroxybutanedioate through Mannich‐type reactions is reported. The reactions take place under mild conditions in good yields, and this makes it possible to introduce various substituents at the α‐position to the P‐atom of α‐aminophosphonates. The chiral diisopropyl (4__R__,5__R__)‐2‐chloro‐1,3,2‐dioxaphospholane‐4,5‐dicarboxylate (3) was found to be a good phosphonylating agent in this stereoselective reaction.

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