Enyne metathesis for the formation of macrocyclic 1,3-dienes

被引：59

作者：

Hansen, EC ^{[1
]}

Lee, DS ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 32期

关键词：

D O I：

10.1021/ja036374k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Macrocyclic 1,3-dienes of a variety of ring sizes are formed in good yield via enyne metathesis. Both endo- and exo-products are observed depending on the size of the macrocycle. In general, 10-membered rings and smaller give exo-products, while 12-membered rings and larger give endo-products. The endo/exo selectivity and the E/Z ratio of the diene products can be further controlled by the presence of ethylene in the reaction. Copyright © 2003 American Chemical Society.

引用

页码：9582 / 9583

页数：2

共 34 条

[1] Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[2] The behavior of 1,n-enynes in the presence of transition metals
Aubert, C
Buisine, O
Malacria, M
[J]. CHEMICAL REVIEWS, 2002, 102 (03) : 813 - 834
[3] Stereoselective radical reactions of some tartaric and glyceric acid derivatives
Barros, MT
Maycock, CD
Ventura, MR
[J]. ORGANIC LETTERS, 2002, 4 (12) : 2035 - 2038
[4] LIVING RING-OPENING METATHESIS POLYMERIZATION OF 2,3-DIFUNCTIONALIZED 7-OXANORBORNENES AND 7-OXANORBORNADIENES BY MO(CHCME2R)(N-2,6-C6H3-ISO-PR2)(O-TERT-BU)2 AND MO(CHCME2R)(N-2,6-C6H3-ISO-PR2)(OCME2CF3)2
BAZAN, GC
OSKAM, JH
CHO, HN
PARK, LY
SCHROCK, RR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) : 6899 - 6907
[5] Recent developments in olefin cross-metathesis
Connon, SJ
Blechert, S
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) : 1900 - 1923
[6] Synthesis of carbohydrate-derived enynes and subsequent metathesis to yield polyhydroxylated 1-vinylcycloalkenes
Dolhem, F
Lièvre, C
Demailly, G
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (12) : 2336 - 2342
[7] Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
[8] Ring closing alkyne metathesis.: Comparative investigation of two different catalyst systems and application to the stereoselective synthesis of olfactory lactones, azamacrolides, and the macrocyclic perimeter of the marine alkaloid nakadomarin A
Fürstner, A
Guth, O
Rumbo, A
Seidel, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) : 11108 - 11113
[9] Fürstner A, 1998, ANGEW CHEM INT EDIT, V37, P1734, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1734::AID-ANIE1734>3.0.CO
[10] 2-6

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