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An Efficient Synthesis of N ‐Phosphorylated Azadienes, Primary ( E )‐Allylamines, and β‐Amino‐Phosphane Oxides and ‐Phosphonates from β‐Functionalized Oxime Derivatives
Author(s) -
Palacios Francisco,
Aparicio Domitila,
García Jesús,
Rodríguez Encina
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199807)1998:7<1413::aid-ejoc1413>3.0.co;2-e
Subject(s) - chemistry , oxime , primary (astronomy) , stereoselectivity , phosphorus , organic chemistry , phosphorylation , combinatorial chemistry , medicinal chemistry , catalysis , biochemistry , physics , astronomy
A simple and stereoselective synthesis of primary ( E )‐allylamines 1 and 1‐azadienes 5 , 7 is reported. N ‐Phosphorylated azadienes 5 and 7 are obtained by addition of phosphorus chlorides 3 to unsaturated oximes 2 , while azadienes 24 are prepared by olefination reactions of functionalized enamines 20/21 . Reduction of azadienes 5 , 7 , 24 and derivatives 13 / 14 and 20/21 with hydrides, followed by deprotection of the resulting amines leads to the formation of primary allylamines 1 and β‐aminophosphane oxides 17 , phosphonates 18 , and phosphonic acid derivatives 19 .