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First Synthesis of ( R )‐ and ( S )‐1,2,3,4‐Tetrahydroisoquinoline‐3‐phosphonic Acid (Tic P ) Using a Pictet–Spengler Reaction
Author(s) -
ViverosCeballos José Luis,
Ordóñez Mario,
Sayago Francisco J.,
Jiménez Ana I.,
Cativiela Carlos
Publication year - 2016
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/ejoc.201600313
Subject(s) - tetrahydroisoquinoline , chemistry , pictet–spengler reaction , phosphonate , yield (engineering) , stereochemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
We report here a practical and efficient synthesis of diethyl 1,2,3,4‐tetrahydroisoquinoline‐3‐phosphonate derivatives. The target compounds were prepared in good yield using a Pictet–Spengler reaction involving α‐amino phosphonates that were easily obtained. We have paid special attention to the synthesis of ( R )‐ and ( S )‐1,2,3,4‐tetrahydroisoquinoline‐3‐phosphonic acid (Tic P ) 2a , a conformationally constrained analogue of phosphophenylalanine Phe P . The procedure is based on the preparation of racemic phosphophenylalanine (Phe P ) diethyl ester followed by chiral chromatographic separation and subsequent Pictet–Spengler chemistry.