Highly reactive and chemoselective cleavage of allyl esters using an air- and moisture-stable [CpRu(IV)(π-C3H5)(2-quinolinecarboxylato)]PF6 catalyst

被引:23
作者
Tanaka, Shinji
Saburi, Hajime
Murase, Takanori
Ishibashi, Yoshitaka
Kitamura, Masato [1 ]
机构
[1] Nagoya Univ, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Dept Chem, Nagoya, Aichi 4648602, Japan
关键词
deallylation; alcoholic solvent; allyl ester; ruthenium; pi-allyl complex;
D O I
10.1016/j.jorganchem.2006.03.046
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new catalytic process for allyl ester cleavage has been developed by using a robust cationic CpRu(TV) pi-allyl complex of 2-quinolinecarboxylic acid that can be stored for over six months in air without any loss of catalytic activity. The deprotection of various alcohols and acids can be attained simply with high reactivity and chemoselectivity under mild conditions. Furthermore, with continuous removal of the low-boiling point coproduct, a turnover number of 1000000 can be achieved. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:295 / 298
页数:4
相关论文
共 30 条
[1]   Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides [J].
Baeschlin, DK ;
Green, LG ;
Hahn, MG ;
Hinzen, B ;
Ince, SJ ;
Ley, SV .
TETRAHEDRON-ASYMMETRY, 2000, 11 (01) :173-197
[2]  
COREY EJ, 1977, TETRAHEDRON LETT, P2081
[3]   CLEAVAGE OF ALLYLOXYCARBONYL PROTECTING GROUP FROM OXYGEN AND NITROGEN UNDER MILD CONDITIONS BY NICKEL CARBONYL [J].
COREY, EJ ;
SUGGS, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (18) :3223-3224
[4]   SELECTIVE CLEAVAGE OF THE ALLYL AND ALLYLOXCARBONYL GROUPS THROUGH PALLADIUM-CATALYZED HYDROSTANNOLYSIS WITH TRIBUTYLTIN HYDRIDE - APPLICATION TO THE SELECTIVE PROTECTION-DEPROTECTION OF AMINO-ACID DERIVATIVES AND IN PEPTIDE-SYNTHESIS [J].
DANGLES, O ;
GUIBE, F ;
BALAVOINE, G ;
LAVIELLE, S ;
MARQUET, A .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4984-4993
[5]   STEREOSELECTIVITY AND REGIOSELECTIVITY IN PALLADIUM-CATALYZED ALLYLIC ETHERIFICATION [J].
GOUX, C ;
MASSACRET, M ;
LHOSTE, P ;
SINOU, D .
ORGANOMETALLICS, 1995, 14 (10) :4585-4593
[6]  
GREEN TW, 1999, PROTECTIVE GROUPS OR
[7]   Preparation of 'side-chain-to-side-chain' cyclic peptides by Allyl and Alloc strategy: potential for library synthesis [J].
Grieco, P ;
Gitu, PM ;
Hruby, VJ .
JOURNAL OF PEPTIDE RESEARCH, 2001, 57 (03) :250-256
[8]   THE ALLYLOXYCARBONYL GROUP FOR ALCOHOL PROTECTION - QUANTITATIVE REMOVAL OR TRANSFORMATION INTO ALLYL PROTECTING GROUP VIA PI-ALLYL COMPLEXES OF PALLADIUM [J].
GUIBE, F ;
SAINTMLEUX, Y .
TETRAHEDRON LETTERS, 1981, 22 (37) :3591-3594
[9]   Allylic protecting groups and their use in a complex environment -: Part II:: Allylic protecting groups and their removal through catalytic palladium π-allyl methodology [J].
Guibé, F .
TETRAHEDRON, 1998, 54 (13) :2967-3042
[10]   Acid/azole complexes as highly effective promoters in the synthesis of DNA and RNA oligomers via the phosphoramidite method [J].
Hayakawa, Y ;
Kawai, R ;
Hirata, A ;
Sugimoto, J ;
Kataoka, M ;
Sakakura, A ;
Hirose, M ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) :8165-8176