An efficient preparation of 3-azabicyclo [3.3.0]. Oct-5-en-7-ones from propargyl alcohol- cobalt complexes via nicholas reaction with amidic nitrogen nucleophiles followed by pauson-khand cyclization

Nakcheol Jeong, Sung eun Yoo, Sang Jo Lee, Sang Hee Lee, Young Keun Chung

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55 Citations (Scopus)

Abstract

3-Azabicyclo [3.3.0]-oct-5-en-7-ones were efficiently prepared from cobalt-propagyl alcohol complexes and various allyl amides via Nicholas reaction in the presence of BF3Et2O followed by Pauson-Khand cyclization promoted with trimethylamine N-oxide or SiO2.

Original languageEnglish
Pages (from-to)2137-2140
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number19
DOIs
Publication statusPublished - 1991 May 6

Bibliographical note

Funding Information:
1984,25,1425f.o r the racemic one see, V as, D.M.; Ching,Y,; Doyle,T.W. J.Org.Chem. 19&149, 2037, We have employed racemic vinyl g ry cme in this study for the determination of diastereose-lectivit 11. Usua Ply trialkylamine N-oxide accelerated the cyclization too much to ‘ve a good stereoselectivity. For example, the reaction between a&me-cobalt complex and norborna 8 ene gave a mixture of cm and endo( ca 85:15) umducts under this condition. while thermal reaction &orded an em Droduct ex-clusively. ‘Refer ref 5. 12. Magnus, P.; Principe, L.M. TetrahedronL &t. 1985,26,4851N.o good reasons for the beneficial effects of MOM ups are provided yet. 13. Completion oft %”e total synthesis starting with the optically active vinyl glycine is in pmgress and will be published elsewhere. 14. At this stage, bishexacarbonyldicobaltacet lene ether (‘H NMR (C D,); d. 1.10 (6 H, d, J = 6.3Hx), 2.80 (2 H, m), 5.5 (2 H, br s)) was formed ( &r - 0.7 compared to R&3 for the pm argyl alcohol-cobalt compex in hexane-ethyl acetate= 2:1), which was purified and characterize 3 but subjected to the nucleo hilic addition with amides directly. 15. N.J.,S.H. P,. , S.J.L., S.e.Y. thank the Ministry of Science and Technolo of Korea for financial sup ort and Y.K.C. thanks the Ministry of Education of Korea for fmancia P support through the Basic 6.l cence Research Institute Pmgram(l990).

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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