Stereoselective synthesis of trans beta-lactams via palladium/N-heterocyclic carbene-catalyzed carbonylative [2+2] cycloaddition

doi:10.1016/j.tetlet.2012.01.073

	Stereoselective synthesis of trans beta-lactams via palladium/N-heterocyclic carbene-catalyzed carbonylative [2+2] cycloaddition
Department	OSSO国家重点实验室
	Jie P(解攀); Qian B(钱波); Huang HM(黄汉民); Xia CG(夏春谷); Huang HM(黄汉民); Xia CG(夏春谷)
	2012
Source Publication	Tetrahedron Letters
ISSN	0040-4039
Volume	53 Issue:13 Pages:1613-1616
Abstract	The carbonylative [2+2] cycloaddition of benzyl chlorides and allyl derivatives with imines and CO for synthesis of β-lactam is effectively catalyzed by palladium/N-heterocyclic carbene complex. The desired β-lactam could be obtained in good to excellent yields (61–96%) with excellent regioselectivities (trans/cis > 95:5) and chiral lactams could be obtained with moderate diastereoselectivities. The KIE experimental studies have revealed that the C–H cleavage is most likely to be the rate-limiting step for the carbonylative cycloaddition.
Keyword	Trans-beta-lactam N-heterocyclic Carbene Palladium Carbonylative [2+2] Cycloaddition
Subject Area	物理化学与绿色催化
DOI	10.1016/j.tetlet.2012.01.073
Funding Organization	the Chinese Academy of Sciences;National Natural Science Foundation of China (20802085)
Indexed By	SCI
If	2.397
Language	英语
Funding Project	有机功能材料研究组;均相催化课题组
compositor	第一作者单位
Citation statistics	Cited Times:19[WOS] [WOS Record] [Related Records in WOS]
Document Type	期刊论文
Identifier	http://ir.licp.cn/handle/362003/3880
Collection	羰基合成与选择氧化国家重点实验室（OSSO）
Corresponding Author	Huang HM(黄汉民); Xia CG(夏春谷)
Affiliation	Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
Recommended Citation GB/T 7714	Jie P,Qian B,Huang HM,et al. Stereoselective synthesis of trans beta-lactams via palladium/N-heterocyclic carbene-catalyzed carbonylative [2+2] cycloaddition[J]. Tetrahedron Letters,2012,53(13):1613-1616.
APA	Jie P,Qian B,Huang HM,Xia CG,黄汉民,&夏春谷.(2012).Stereoselective synthesis of trans beta-lactams via palladium/N-heterocyclic carbene-catalyzed carbonylative [2+2] cycloaddition.Tetrahedron Letters,53(13),1613-1616.
MLA	Jie P,et al."Stereoselective synthesis of trans beta-lactams via palladium/N-heterocyclic carbene-catalyzed carbonylative [2+2] cycloaddition".Tetrahedron Letters 53.13(2012):1613-1616.

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