Synthesis of Enantiomerically Enriched Indolines and Tetrahydroisoquinolines from (S)-Amino Acid-Derived Chiral Carbocations: An Easy Access to (3S,4R)-Demethoxy-3-isopropyl Diclofensine

Manna, S K; Panda, Gautam

dc.contributor.author	Manna, S K
dc.contributor.author	Panda, Gautam
dc.date.accessioned	2017-06-13T07:46:39Z
dc.date.available	2017-06-13T07:46:39Z
dc.date.issued	2014
dc.identifier.citation	Org. Biomol. Chem., 2014, 12, 8318–8324	en
dc.identifier.uri	http://hdl.handle.net/123456789/1702
dc.description.abstract	Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized within 5 min to 2 h in high yields from easily accessible (S)-amino acids derived chiral carbocations. The diastereoselective Friedel-Crafts reaction is promoted by Lewis acid (AlCl3) offering trans-diastereoselectivity. The rate of the reaction and diastereoselectivity of the product are significantly influenced by steric hindrance of substituents of amino acids and aryl groups. The methodology can be applied for the synthesis of enantiomercally enriched bioactive scaffold (3S, 4R)-demethoxy-3-isopropyl diclofensine.	en
dc.format.extent	360128 bytes
dc.format.mimetype	application/pdf
dc.language.iso	en	en
dc.relation.ispartofseries	CSIR-CDRI Communicationno. 8787	en
dc.subject	Indolines	en
dc.subject	Tetrahydroisoquinolines	en
dc.subject	Chiral carbocations	en
dc.subject	Friedel-Crafts cyclization	en
dc.title	Synthesis of Enantiomerically Enriched Indolines and Tetrahydroisoquinolines from (S)-Amino Acid-Derived Chiral Carbocations: An Easy Access to (3S,4R)-Demethoxy-3-isopropyl Diclofensine	en
dc.type	Article	en