Gold-Catalyzed Stereoselective Synthesis of Bicyclic Lactams and Ketones from N-Tosylynamidomethyl-Tethered Cyclohexenes

Chang Zhi Zhong, Po Ting Tung, Tsung Han Chao, Ming-Chang P. Yeh

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Six-membered ring 3-enynamides underwent cycloisomerization in the presence of a catalytic amount of a gold(I) complex delivering mainly 4-azatricyclo[4.3.1.03,10]dec-2-ene derivatives and dibenz[cd,f]indole derivatives as the minor products under mild reaction conditions. Upon exposure to air, most aryl-substituted azatricycles led to bicyclic γ-lactams, while the ortho-tolyl- or alkyl-substituted azatricycles provided the corresponding bicyclic γ-lactams after oxidation with osmium tetraoxide and N-methylmorpholine-N-oxide. Under acidic conditions, the ortho-tolyl- or alkyl-substituted azatricycles were further transformed into 5-N-tosylaminomethyl-tethered bicyclo[4.2.0]octan-7-ones. The gold(I)-catalyzed tandem cycloisomerization/oxidation reaction also provided a new route for the synthesis of bridged bicyclic δ-lactams from six-membered ring 4-enynamides. The mild reaction conditions allowed the synthesis of a range of bicyclic γ- and δ-lactams and N-tosylaminomethyl-tethered bicyclo[4.2.0]octan-7-ones with high diastereoselectivities.

Original languageEnglish
Pages (from-to)481-501
Number of pages21
JournalJournal of Organic Chemistry
Volume82
Issue number1
DOIs
Publication statusPublished - 2017 Jan 6

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Cyclohexenes
Lactams
Ketones
Gold
Derivatives
Osmium
Oxidation
Air

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Gold-Catalyzed Stereoselective Synthesis of Bicyclic Lactams and Ketones from N-Tosylynamidomethyl-Tethered Cyclohexenes. / Zhong, Chang Zhi; Tung, Po Ting; Chao, Tsung Han; Yeh, Ming-Chang P.

In: Journal of Organic Chemistry, Vol. 82, No. 1, 06.01.2017, p. 481-501.

Research output: Contribution to journalArticle

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