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Volumn 62, Issue 18, 2006, Pages 4331-4341

A new convergent and stereoselective synthesis of 2,5-disubstituted N-acylpyrrolidines

Author keywords

Peptidomimetics; Pyrrolidine; SN2

Indexed keywords

1 ACETYL 2 HYDROXYMETHYL 5 VINYLPYRROLIDINE; 2 ACETOMETHYL 1 ACETYL 4 VINYLPYRROLIDINE; 2,5 BIS(ACETOXYMETHYL) 1 ACETYLPYRROLIDINE; ALLYL COMPOUND; AMIDE; ANION; BROMINE DERIVATIVE; ETHYL 1 ACETYL 5 VINYLPYRROLIDINE 2 CARBOXYLATE; NITROGEN; PYRROLIDINE DERIVATIVE; TERT BUTYL 1 ACETYL 5 VINYLPYRROLIDINE 2 CARBOXYLATE; UNCLASSIFIED DRUG;

EID: 33646106934     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.073     Document Type: Article
Times cited : (9)

References (39)
  • 25
    • 33646095701 scopus 로고    scopus 로고
    • Preliminary data on this work were presented at the 2nd International Conference on Multi Component Reactions, Combinatorial and Related Chemistry (MCR2003), Genova (I), April 14-16, 2003.
  • 27
    • 33646108782 scopus 로고    scopus 로고
    • note
    • The triple bond is versatile since it can be exploited as precursor of both Z and E alkenes.
  • 29
    • 33646080304 scopus 로고    scopus 로고
    • note
    • For minimizing the elimination we usually preferred to stop the reaction before all 13 was consumed, since it was easily recovered and recycled.
  • 30
    • 33646101427 scopus 로고    scopus 로고
    • note
    • Treatment with TsCl in pyridine did not promote any reaction and for this reason we added 4-dimethylaminopyridine.
  • 32
    • 33646085965 scopus 로고    scopus 로고
    • note
    • Since 24 and 25 are racemic, the absolute configuration of them was arbitrarily reported in Scheme 5.
  • 33
    • 33646098107 scopus 로고    scopus 로고
    • note
    • It is noteworthy that, in order to get the highest reproducibility in the synthesis of 24a,b on preparative scale from 21, the reaction has to be performed employing a solution of LiHMDS in THF, freshly prepared by dissolving solid commercial LiHMDS.
  • 37
    • 33646086189 scopus 로고    scopus 로고
    • note
    • The whole sequence was first tested on the 70:30 diastereomeric mixture of 24a,b, to give 29a,b without appreciable changes in dr and then on the separated diastereoisomers.
  • 38
    • 33646105559 scopus 로고    scopus 로고
    • note
    • Intermediate monoalcohol was difficult to be recovered by extractive work up, due to its high affinity for water, and since it was nearly impossible to evidentiate its spot on TLC.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.