Mercuric triflate catalyzed hydroxylative carbocyclization of 1,6-enynes

被引：67

作者：

Nishizawa, M ^{[1
]}

Yadav, VK ^{[1
]}

Skwarczynski, M ^{[1
]}

Takao, H ^{[1
]}

Imagawa, H ^{[1
]}

Sugihara, T ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Tokushima 7708514, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 10期

关键词：

D O I：

10.1021/ol034201u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Hg(OTf)(2) exhibits remarkable catalytic activity for the hydroxylative cyclization of 1,6-enynes. The present procedure should involve a sequence of mercuration of a terminal alkyne, carbocyclization, hydration, and protodemercuration that regenerates the catalyst.

引用

页码：1609 / 1611

页数：3

共 42 条

[31]

NISHIZAWA M, 1995, SYNLETT, P169

[32] A NEW OLEFIN CYCLIZATION AGENT, MERCURY(II) TRIFLUOROMETHANESULFONATE AMINE COMPLEX [J].

NISHIZAWA, M ;

TAKENAKA, H ;

NISHIDE, H ;

HAYASHI, Y .

TETRAHEDRON LETTERS, 1983, 24 (25) :2581-2584

[33] Transition metal-catalyzed carbocyclizations in organic synthesis [J].

Ojima, I ;

Tzamarioudaki, M ;

Li, ZY ;

Donovan, RJ .

CHEMICAL REVIEWS, 1996, 96 (02) :635-662

[34] THE FIRST TOTAL SYNTHESIS OF A PYRIPYROPENE-TYPE ACAT INHIBITOR, (+/-)-GERI-BP001 [J].

PARKER, KA ;

RESNICK, L .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5726-5728

[35] MERCURY(II)-INDUCED CYCLIZATION OF ACETYLENIC ALCOHOLS - A NEW ROUTE TO ENOL ETHERS AND SUBSTITUTED ENOL ETHERS [J].

RIEDIKER, M ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (21) :5842-5844

[36] A titanocene-catalyzed intramolecular ene reaction: Cycloisomerization of enynes and dienynes [J].

Sturla, SJ ;

Kablaoui, NM ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) :1976-1977

[37] Ruthenium-catalyzed cycloisomerization of 1,6-enynes initiated by C-H activation [J].

Trost, BM ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9728-9729

[38] Ruthenium-catalyzed cycloisomerizations of 1,6- and 1,7-enynes [J].

Trost, BM ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (04) :714-715

[39]

Trost BM, 1998, CHEM-EUR J, V4, P2405, DOI 10.1002/(SICI)1521-3765(19981204)4:12<2405::AID-CHEM2405>3.0.CO

[40]

2-0

← 1 2 3 4 5 →