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A General Method for the Preparation of Chiral TREN Derivatives
Author(s) -
Pei Yuxin,
Brade Katja,
Brulé Emilie,
Hagberg Lars,
Lake, Fredrik,
Moberg Christina
Publication year - 2005
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.200500094
Subject(s) - chemistry , regioselectivity , yield (engineering) , ring (chemistry) , chirality (physics) , amino acid , alcohol , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , metallurgy , quark , materials science
Abstract A general procedure for the preparation of C 3 ‐symmetric TREN derivatives with backbone chirality has been developed. Stereo‐ and regioselective ring opening by ammonia of ( S )‐ N ‐tosyl‐2‐isopropylaziridine, obtained starting from either the corresponding amino alcohol or amino acid, followed by deprotection of the amino groups afforded the parent chiral TREN compound in high overall yield. In addition to TREN compounds with primary amino groups, the synthetic method employed provides easy access to a variety of N , N' , N'' ‐substituted derivatives. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)