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Syntheses of α‐Aminophosphonic Acids, VI. Synthesis of Diastereomerically Pure 1‐Aminocyclopropylphosphonic Acids
Author(s) -
Groth Ulrich,
Lehmann Lutz,
Richter Lutz,
Schöllkopfh Ulrich
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930169
Subject(s) - chemistry , diethyl ether , boron trifluoride , hydrolysis , trimethylsilyl , potassium , yield (engineering) , base (topology) , lithium (medication) , organic chemistry , iodide , boron , derivative (finance) , medicinal chemistry , iodine , catalysis , medicine , mathematical analysis , materials science , mathematics , economics , financial economics , metallurgy , endocrinology
The lithium or potassium derivative of diethyl isocyanomethylphosphonate ( 1 ) reacts with epoxides in the presence of boron trifluoride–diethyl ether to provide the diethyl 3‐hydroxy‐1‐isocyanoalkylphosphonates rac ‐ 3 . The corresponding mesylates rac ‐ 4 undergo a base‐mediated cyclization to the diethyl 1‐isocyanocyclopropylphosphonates rac ‐ 5 . Acidic hydrolysis affords the diethyl 1‐aminocyanocyclopropylphosphonates rac ‐ 6 , which upon treatment with trimethylsilyl iodide yield the 1‐aminocyclopropylphosphonic acids rac ‐ 7 . A base‐mediated cycloalkylation of 1 with dibromoalkanes 10 gives the diethyl 1‐isocyanocycloalkylphosphonates 11 , which are suitable precursors for the achiral 1‐aminocycloalkylphosphonic acids.