Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes

被引：118

作者：

Corkey, Britton K. ^{[1
]}

Toste, F. Dean ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 10期

关键词：

D O I：

10.1021/ja068723r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective intramolecular addition of silyl enol ethers and silyl ketene aminals onto alkyne is described. The reaction employs DTBMSegphos-Pd(II) or Binaphane-Pd(II) complexes as catalysts for the formation of methylene cyclopentane adducts from 1,6-enyne precursors. The utility of this reaction is illustrated by its application to the total synthesis of the cytotoxic cyclolaurane-type sesquiterpene, (-)-laurebiphenyl.

引用

页码：2764 / +

页数：3

共 40 条

[1] Bonding modes in palladium(II) enolates:: Consequences for dynamic behavior and reactivity
Albéniz, AC
Catalina, NM
Espinet, P
Redón, R
[J]. ORGANOMETALLICS, 1999, 18 (26) : 5571 - 5576
[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] SYNTHESIS AND REACTIONS OF NICKEL AND PALLADIUM CARBON-BOUND ENOLATE COMPLEXES
BURKHARDT, ER
BERGMAN, RG
HEATHCOCK, CH
[J]. ORGANOMETALLICS, 1990, 9 (01) : 30 - 44
[4] Cao P, 2000, ANGEW CHEM INT EDIT, V39, P4104, DOI 10.1002/1521-3773(20001117)39:22<4104::AID-ANIE4104>3.0.CO
[5] 2-X
[6] Functionalized carbo- and heterocycles via Pt-catalyzed asymmetric alkoxycyclization of 1,6-enynes
Charruault, L
Michelet, V
Taras, R
Gladiali, S
Genêt, JP
[J]. CHEMICAL COMMUNICATIONS, 2004, (07) : 850 - 851
[7] Catalytic enantioselective Conia-ene reaction
Corkey, BK
Toste, FD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) : 17168 - 17169
[8] Asymmetric cycloisomerization of 1,6-and 1,7-enynes by transition-metal catalysts
Fairlamb, IJS
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) : 1048 - 1052
[9] Modular catalysts for diene cycloisomerization:: Rapid and enantioselective variants for bicyclopropane synthesis
Feducia, Jeremy A.
Campbell, Alison N.
Doherty, Michael Q.
Gagne, Michel R.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) : 13290 - 13297
[10] Mechanism of palladium complex-catalyzed enantioselective Mannich-type reaction: Characterization of a novel binuclear palladium enolate complex
Fujii, A
Hagiwara, E
Sodeoka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (23) : 5450 - 5458

← 1 2 3 4 →