Stereoselective synthesis of dipeptide β-turn mimetics

7-Benzyl and 8-phenyl substituted azabicyclo[4.3.0]nonane amino acid esters

Wei Wang, Jianqing Yang, Jinfa Ying, Chiyi Xiong, Junyi Zhang, Chaozhong Cai, Victor J Hruby

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

A stereoselective method has been developed for the synthesis of 7- and 8-substituted dipeptide β-turn mimetic azabicyclo[4.3.0]nonane amino acid esters. The allyl groups were introduced in high diastereoselectivity, controlled by 3-phenyl or 4-benzyl groups in pyroglutamic acid derivatives 3 or 9, respectively. The precursors, dehydroamino acids 7 and 13 derived from 5 or 11, underwent asymmetric hydrogenations with Burk's DuPHOS Rh(I)-based catalysts to furnish α-amino acid derivatives in high stereoselectivity. The resulting amino acids 8 and 14 were converted to the β-turn mimetics 6,5-bicyclic lactams 1a-d in high yields.

Original languageEnglish (US)
Pages (from-to)6353-6360
Number of pages8
JournalJournal of Organic Chemistry
Volume67
Issue number18
DOIs
StatePublished - Sep 6 2002

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Azabicyclo Compounds
Dipeptides
Esters
Amino Acids
Pyrrolidonecarboxylic Acid
Derivatives
Stereoselectivity
Lactams
Hydrogenation
Catalysts
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective synthesis of dipeptide β-turn mimetics : 7-Benzyl and 8-phenyl substituted azabicyclo[4.3.0]nonane amino acid esters. / Wang, Wei; Yang, Jianqing; Ying, Jinfa; Xiong, Chiyi; Zhang, Junyi; Cai, Chaozhong; Hruby, Victor J.

In: Journal of Organic Chemistry, Vol. 67, No. 18, 06.09.2002, p. 6353-6360.

Research output: Contribution to journalArticle

Wang, Wei ; Yang, Jianqing ; Ying, Jinfa ; Xiong, Chiyi ; Zhang, Junyi ; Cai, Chaozhong ; Hruby, Victor J. / Stereoselective synthesis of dipeptide β-turn mimetics : 7-Benzyl and 8-phenyl substituted azabicyclo[4.3.0]nonane amino acid esters. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 18. pp. 6353-6360.
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