A rhodium(I)-catalyzed formal allenic Alder ene reaction for the rapid and stereoselective assembly of cross-conjugated trienes

被引：156

作者：

Brummond, KM ^{[1
]}

Chen, HF ^{[1
]}

Sill, P ^{[1
]}

You, LF ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 51期

关键词：

D O I：

10.1021/ja027588p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium(I)-catalyzed allenic Alder ene reaction to prepare cross-conjugated trienes has been discovered. The scope and limitations are currently being investigated, and the results obtained to date are reported on. This method shows enticing functional group compatibility by tolerating terminal and internal alkynes, hydroxyl, sulfonamide, ether, and diester groups. Progress has been made to increase the stereoselectivity of the olefinic side chain via an unprecendented iridium(I) catalyzed Alder-ene reaction. Copyright © 2002 American Chemical Society.

引用

页码：15186 / 15187

页数：2

共 21 条

[1] 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
[2] An allenic Pauson-Khand-type reaction:: A reversal in π-bond selectivity and the formation of seven-membered rings
Brummond, KM
Chen, HF
Fisher, KD
Kerekes, AD
Rickards, B
Sill, PC
Geib, SJ
[J]. ORGANIC LETTERS, 2002, 4 (11) : 1931 - 1934
[3] A silicon-tethered allenic Pauson-Khand reaction
Brummond, KM
Sill, PC
Rickards, B
Geib, SJ
[J]. TETRAHEDRON LETTERS, 2002, 43 (20) : 3735 - 3738
[4] Rh-catalyzed enyne cycloisomerization
Cao, P
Wang, B
Zhang, XM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) : 6490 - 6491
[5] First examples of cobalt-mediated formal Alder ene reaction of allenynes.
Llerena, D
Aubert, C
Malacria, M
[J]. TETRAHEDRON LETTERS, 1996, 37 (39) : 7027 - 7030
[6] Chemoselectivities in palladium- and rhodium-catalyzed allenyne cyclizations
Oh, CH
Jung, SH
Rhim, CY
[J]. TETRAHEDRON LETTERS, 2001, 42 (49) : 8669 - 8671
[7] Pagenkopf BL, 2000, SYNTHESIS-STUTTGART, P1009
[8] ENANTIOSELECTIVE SYNTHESIS OF AN ADVANCED INTERMEDIATE TO QUASSINOIDS
SPINO, C
TU, N
[J]. TETRAHEDRON LETTERS, 1994, 35 (22) : 3683 - 3686
[9] THE DIENE-TRANSMISSIVE [4+2]-CYCLOADDITION STRATEGY - STEREOSELECTIVE SYNTHESIS OF ADVANCED INTERMEDIATES TO QUASSINOIDS
SPINO, C
LIU, G
TU, N
GIRARD, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) : 5596 - 5608
[10] A titanocene-catalyzed intramolecular ene reaction: Cycloisomerization of enynes and dienynes
Sturla, SJ
Kablaoui, NM
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) : 1976 - 1977

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