An Intramolecular 1,3‐Dipolar Cycloaddition Involving One Alkyne and Two Nitrone Groups | Zendy

Aurich Hans Günter | Zendy; Biesemeier Frank | Zendy; Harms Klaus | Zendy

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An Intramolecular 1,3‐Dipolar Cycloaddition Involving One Alkyne and Two Nitrone Groups

Author(s) -

Aurich Hans Günter,

Biesemeier Frank,

Harms Klaus

Publication year - 1997

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199719970306

Subject(s) - intramolecular force , chemistry , nitrone , cycloaddition , alkyne , ring (chemistry) , medicinal chemistry , stereochemistry , organic chemistry , catalysis

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 .

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