Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters

被引：156

作者：

Prasad, BAB ^{[1
]}

Yoshimoto, FK ^{[1
]}

Sarpong, R ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 36期

关键词：

D O I：

10.1021/ja053192c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly selective and efficient Pt-catalyzed pentannulation reaction beginning from propargylic esters is described. The key to this reaction is the use of a PtCl2(PPh3)2/PhIO catalyst combination that allows the in situ generation of Pt-carbenoid intermediates, which lead to good yields (61-84%) of the desired pentannulated compounds. Copyright © 2005 American Chemical Society.

引用

页码：12468 / 12469

页数：2

共 19 条

[1] Tandem PtCl2 catalyzed-thermal [3,3] rearrangements of enyne acetates
Cariou, K
Mainetti, E
Fensterbank, L
Malacria, M
[J]. TETRAHEDRON, 2004, 60 (43) : 9745 - 9755
[2] Rapid assembly of substituted dihydrocyclohepta[3,4] pyrrolo[1,2-a]indoles via a novel, carbene-based, rearrangement reaction
Frey, LF
Tillyer, RD
Ouellet, SG
Reamer, RA
Grabowski, EJJ
Reider, PJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) : 1215 - 1216
[3] Platinum-catalyzed cycloisomerization reactions of enynes
Fürstner, A
Stelzer, F
Szillat, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) : 11863 - 11869
[4] Habermas K.L., 1994, ORG REACTIONS, V45, P1
[5] PtCl2-catalyzed cycloisomerizations of 5-En-1-yn-3-ol systems
Harrak, Y
Blaszykowski, C
Bernard, M
Cariou, K
Mainetti, E
Mouriès, V
Dhimane, AL
Fensterbank, L
Malacria, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) : 8656 - 8657
[6] THERMAL CYCLIZATION OF ALPHA-ALKYNONES TO 2-CYCLOPENTENONES
KARPF, M
DREIDING, AS
[J]. HELVETICA CHIMICA ACTA, 1979, 62 (03) : 852 - 865
[7] Transition metal salts-catalyzed aza-Michael reactions of enones with carbamates
Kobayashi, S
Kakumoto, K
Sugiura, M
[J]. ORGANIC LETTERS, 2002, 4 (08) : 1319 - 1322
[8] Mainetti E, 2002, ANGEW CHEM INT EDIT, V41, P2132, DOI 10.1002/1521-3773(20020617)41:12<2132::AID-ANIE2132>3.0.CO
[9] 2-S
[10] Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes
Mamane, V
Gress, T
Krause, H
Fürstner, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) : 8654 - 8655

← 1 2 →