TY - JOUR
T1 - Catalytic diamination of alkenes using N,N-dibromo-p-toluenesulfonamide as electrophile and nitriles as nucleophiles
AU - Han, Jianlin
AU - Li, Tengfei
AU - Pan, Yi
AU - Kattuboina, Adiseshu
AU - Li, Guigen
N1 - Copyright:
Copyright 2009 Elsevier B.V., All rights reserved.
PY - 2008/1
Y1 - 2008/1
N2 - An efficient diamination reaction of alkenes has been developed for the synthesis of bromoalkyl-branched imidazolines by using CuI-PPh3 as the catalyst and N,N-dibromo-p-toluenesulfonamide as the nitrogen/halogen sources. A good scope of alkene substrates, including α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins, was achieved for this reaction. Meanwhile, various nitriles were utilized as nucleophilic nitrogen sources. Modest to good yields and excellent regio- and stereoselectivity have been obtained. The stereochemistry was unambiguously confirmed by X-ray structural analysis. A new mild condition was found for the opening of resulting imidazolines by using SnCl4 as the promoter.
AB - An efficient diamination reaction of alkenes has been developed for the synthesis of bromoalkyl-branched imidazolines by using CuI-PPh3 as the catalyst and N,N-dibromo-p-toluenesulfonamide as the nitrogen/halogen sources. A good scope of alkene substrates, including α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins, was achieved for this reaction. Meanwhile, various nitriles were utilized as nucleophilic nitrogen sources. Modest to good yields and excellent regio- and stereoselectivity have been obtained. The stereochemistry was unambiguously confirmed by X-ray structural analysis. A new mild condition was found for the opening of resulting imidazolines by using SnCl4 as the promoter.
KW - Copper iodide
KW - Diamination
KW - Imidazoline
KW - N,N-dibromo-p-toluenesulfonamide
KW - Tin tetrachloride
UR - http://www.scopus.com/inward/record.url?scp=37849007557&partnerID=8YFLogxK
U2 - 10.1111/j.1747-0285.2007.00604.x
DO - 10.1111/j.1747-0285.2007.00604.x
M3 - Article
C2 - 18069987
AN - SCOPUS:37849007557
VL - 71
SP - 71
EP - 77
JO - Chemical Biology and Drug Design
JF - Chemical Biology and Drug Design
SN - 1747-0277
IS - 1
ER -