Synthesis of macrocyclic carbonates with musk odor by ring-closing olefin metathesis

被引：24
作者：
Michrowska, A
Wawrzyniak, P
Grela, K
机构：
[1] Warsaw Univ Technol, Fac Chem, PL-00662 Warsaw, Poland
[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 09期
关键词：
flavors and fragrances; musk; metathesis; macrolides; ruthenium;
D O I：
10.1002/ejoc.200300768
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This study shows the efficiency of modern well-defined ruthenium catalysts for the formation of musk-odored macrocyclic carbonates with ring sizes between 15-23 atoms. It also reveals that, in these cases, geometric factors are very important and that smaller ring carbonates are difficult to ac-cess by ring closing metathesis, even with highly active second-generation rutilenium. catalysts. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
引用
收藏
页码：2053 / 2056
页数：4
相关论文
共 43 条
[1]   Non-metathetic behavior patterns of Grubbs' carbene [J].
Alcaide, B ;
Almendros, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (06) :1259-1262
[2]   A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM ;
Aly, MF .
ORGANIC LETTERS, 2001, 3 (23) :3781-3784
[3]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[4]   Rate studies and mechanism of ring-closing olefin metathesis catalyzed by cationic ruthenium allenylidene arene complexes [J].
Bassetti, M ;
Centola, F .
ORGANOMETALLICS, 2003, 22 (22) :4459-4466
[5]   Enantioselective perception of chiral odorants [J].
Brenna, E ;
Fuganti, C ;
Serra, S .
TETRAHEDRON-ASYMMETRY, 2003, 14 (01) :1-42
[6]  
Brunelle DJ, 1993, RING OPENING POLYM
[7]   Homogeneous metathesis polymerization by well-defined group VI and group VIII transition-metal alkylidenes: Fundamentals and applications in the preparation of advanced materials [J].
Buchmeiser, MR .
CHEMICAL REVIEWS, 2000, 100 (04) :1565-1604
[8]   Olefin isomerization by a ruthenium carbenoid complex. Cleavage of allyl and homoallyl groups [J].
Cadot, C ;
Dalko, PI ;
Cossy, J .
TETRAHEDRON LETTERS, 2002, 43 (10) :1839-1841
[9]  
CAROTHERS WH, 1935, Patent No. 2020298
[10]   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
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