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Ring-chain tautomerism in organic synthesis: synthesis of heterocyclic enamines from a novel and practical formal ring transformation reaction of lactones.

Abstract:

A novel approach to heterocyclic enamines has been developed from the formal ring transformation reaction of lactones. The synthesis comprises consecutive Reformatsky reaction of lactones and mesylation of the resulting mixture of ring-chain tautomers in a one-pot reaction, followed by cyclocondensation reaction with primary amines. The synthetic application of this method was demonstrated by a straightforward preparation of indolizidine compounds via N-(3-bromopropyl)-substituted enamine int...

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Publication status:
Published

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Publisher copy:
10.1021/jo026560t

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Journal:
The Journal of organic chemistry
Volume:
68
Issue:
8
Pages:
3281-3286
Publication date:
2003-04-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:a6039f07-7e3c-45b7-971e-502edec98341
Source identifiers:
38577
Local pid:
pubs:38577
Language:
English

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