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	Synthesis of novel diphosphite ligands derived from d-mannitol and their application in cu-catalyzed enantioselective conjugate addition of organiozinc to enones
	Zhao, Qing-Lu1,2; Wang, Lai-Lai1; Xing, Ai-Ping1,2
刊名	Tetrahedron-asymmetry
	2010-12-20
卷号	21期号:24页码:2993-2998
ISSN号	0957-4166
DOI	10.1016/j.tetasy.2010.12.009
通讯作者	Wang, lai-lai(wll@licp.cas.cn)
英文摘要	A series of novel chiral diphosphite ligands have been synthesized from d-mannitol derivatives and chlorophosphoric acid diary ester, and were successfully employed in the copper catalyzed enantioselective conjugate addition of organozinc reagents diethylzinc and dimethylzinc to cyclic and acyclic enones. the stereochemically matched combination of d-mannitol and (r)-h(8)-binaphthyl in ligand 1,2:5,6-di-o-isopropylidene-3,4-bis[(r)-1,1'-h(8)-binaphthyl-2,2'-diyl] phosphite-d-mannitol was essential to afford 93% ee for 3-ethylcyclohexanone, 92% ee for 3-ethylcyclopentanone, and 90% ee for 3-ethylcycloheptanone in toluene, using cu(otf)(2) as a catalytic precursor. the results clearly indicated that the chiral organocopper reagent exhibited high enantioselectivies for cyclic enones bearing different ring sizes. as for the backbone of this type of ligand, it has been demonstrated that 1,2:5,6-di-o-isopropylidene-d-mannitol was more efficient than 1,2:5,6-di-o-cyclohexylidene-d-mannitol. the sense of the enantiodiscrimination was mainly determined by the configuration of the diaryl phosphite moieties in the 1,4-addition of cyclic enones. (c) 2010 elsevier ltd. all rights reserved.
WOS关键词	CHIRAL PHOSPHORUS LIGANDS ; ACYCLIC ALIPHATIC ENONES ; ASYMMETRIC HYDROGENATION ; CYCLIC ENONES ; 1,4-CONJUGATE ADDITION ; MONOPHOSPHITE LIGANDS ; ORGANOZINC REAGENTS ; PHOSPHITE-OXAZOLINE ; MICHAEL ADDITIONS ; ARYL DIPHOSPHITE
WOS研究方向	Chemistry
WOS类目	Chemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000287295400015
内容类型	期刊论文
URI标识	http://www.corc.org.cn/handle/1471x/2405595
专题	中国科学院大学
通讯作者	Wang, Lai-Lai
作者单位	1.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 2.Chinese Acad Sci, Grad Univ, Beijing 100039, Peoples R China
推荐引用方式 GB/T 7714	Zhao, Qing-Lu,Wang, Lai-Lai,Xing, Ai-Ping. Synthesis of novel diphosphite ligands derived from d-mannitol and their application in cu-catalyzed enantioselective conjugate addition of organiozinc to enones[J]. Tetrahedron-asymmetry,2010,21(24):2993-2998.
APA	Zhao, Qing-Lu,Wang, Lai-Lai,&Xing, Ai-Ping.(2010).Synthesis of novel diphosphite ligands derived from d-mannitol and their application in cu-catalyzed enantioselective conjugate addition of organiozinc to enones.Tetrahedron-asymmetry,21(24),2993-2998.
MLA	Zhao, Qing-Lu,et al."Synthesis of novel diphosphite ligands derived from d-mannitol and their application in cu-catalyzed enantioselective conjugate addition of organiozinc to enones".Tetrahedron-asymmetry 21.24(2010):2993-2998.

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