ICCAS OpenIR
Ring-chain tautomerism in organic synthesis: Synthesis of heterocyclic enamines from a novel and practical formal ring transformation reaction of lactones
Wang, MX; Liu, Y; Gao, HY; Zhang, Y; Yu, CY; Huang, ZT; Fleet, GWJ
2003-04-18
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume68Issue:8Pages:3281-3286
AbstractA 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 intermediates. The use of cheap and readily available materials and reagents under very mild conditions renders this formal ring transformation method practical and applicable in the preparation of various heterocyclic enamines that are the precursors for (poly)hydroxylated alkaloid derivatives.
DOI10.1021/jo026560t
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000182280900037
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:20[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/80094
Collection中国科学院化学研究所
Corresponding AuthorWang, MX
Affiliation1.Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Biol Chem Lab, Beijing 100080, Peoples R China
2.Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England
Recommended Citation
GB/T 7714
Wang, MX,Liu, Y,Gao, HY,et al. Ring-chain tautomerism in organic synthesis: Synthesis of heterocyclic enamines from a novel and practical formal ring transformation reaction of lactones[J]. JOURNAL OF ORGANIC CHEMISTRY,2003,68(8):3281-3286.
APA Wang, MX.,Liu, Y.,Gao, HY.,Zhang, Y.,Yu, CY.,...&Fleet, GWJ.(2003).Ring-chain tautomerism in organic synthesis: Synthesis of heterocyclic enamines from a novel and practical formal ring transformation reaction of lactones.JOURNAL OF ORGANIC CHEMISTRY,68(8),3281-3286.
MLA Wang, MX,et al."Ring-chain tautomerism in organic synthesis: Synthesis of heterocyclic enamines from a novel and practical formal ring transformation reaction of lactones".JOURNAL OF ORGANIC CHEMISTRY 68.8(2003):3281-3286.
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