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An Intramolecular 1,3-Dipolar Cycloaddition Involving One Alkyne and Two Nitrone Groups (1997)

Aurich, Hans Günter ; Biesemeier, Frank ; Harms, Klaus

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 469-471

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ISSN: 0947-3440

Keywords: Cycloadditions ; Asymmetric Synthesis ; Heterocycles ; Alkynes ; Reductions ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The chiral nonracemic compound 4 was prepared from ethyl (S)-(-)-lactate and 1,4-dibromo-2-butyne. Reduction with DIBAH at -72°C and subsequent treatment of the resulting dialdehyde with N-methylhydroxylamine yielded the dinitrone 5, which underwent two consecutive intramolecular cycloadditions to give the chiral nonracemic compound 7. The structure of 7 was confirmed by an X-ray analysis. Reductive ring opening afforded compound 8.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970306

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