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Asymmetric Mannich ‐Type Synthesis of N ‐Phosphinyl α ‐Aminophosphonic Acid Monoesters
Author(s) -
Fang Zhijia,
Yang Haohao,
Miao Zhiwei,
Chen Ruyu
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100025
Subject(s) - chemistry , stereoselectivity , mannich reaction , aryl , stereochemistry , medicinal chemistry , catalysis , organic chemistry , alkyl
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.