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O ‐(2‐Oxopyrrolidin‐5‐yl)trichloroacetimidates as Amidoalkylating Agents − Synthesis of (+)‐Lentiginosine
Author(s) -
ElNezhawy Ahmed O. H.,
ElDiwani Hoda I.,
Schmidt Richard R.
Publication year - 2002
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 - 10.1002/1099-0690(200212)2002:24<4137::aid-ejoc4137>3.0.co;2-x
Subject(s) - chemistry , epimer , nucleophile , amide , medicinal chemistry , double bond , ring (chemistry) , stereochemistry , trimethylsilane , alkylation , organic chemistry , catalysis
N ‐α‐Hydroxyalkylamides 6a , b , readily available from L ‐tartrate, with trichloroacetonitrile furnish O ‐(2‐oxopyrrolidin‐5‐yl)trichloroacetimidates 3a , b . α‐Amido‐alkylation studies of 3a , b with allyl‐trimethylsilane and electron‐rich benzene derivatives as C ‐nucleophiles afforded 5‐allyl‐ and 5‐aryl‐2‐pyrrolidinones 2a , b , 7a , b , and 8−10 . The target compound (+)‐ 1 and its epimer 15 were readily obtained from 1,5‐diallyl‐2‐pyrrolidinones 2b and 7b , respectively, via ring‐closing metathesis, amide group reduction, and CC‐double bond hydrogenation. (© Wiley‐VCH Verlag GmbH & Co KGaA, 69451 Weinheim, Germany, 2002)