Gold-catalyzed intramolecular carbocyclization of alkynyl ketones leading to highly substituted cyclic enones

被引：143

作者：

Jin, Tienan ^{[1
]}

Yamamoto, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 25期

关键词：

D O I：

10.1021/ol702455v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the internal alkynyl ketones 1 (n = 1) under the combined catalyst, AUCl(3) and AgSbF6, gave the enones 2 in good to high yields, whereas that of the terminal alkynyl ketones 1 (n = 0) under the combined catalyst, AuCl3 and AgOTf, afforded the cyclic enones 3.

引用

页码：5259 / 5262

页数：4

共 37 条

[1] Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines [J].

Asao, N ;

Yudha, S ;

Nogami, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5526-5528

[2] AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].

Asao, N ;

Aikawa, H ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459

[3] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].

Asao, N ;

Nogami, T ;

Lee, S ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925

[4] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[5] TRANSANNULAR CYCLIZATIONS OF 6-SUBSTITUTED CYCLODECYNES [J].

BALF, RJ ;

RAO, B ;

WEILER, L .

CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (19) :3135-&

[6] ADDITIVE AND MEDIUM EFFECTS ON LEWIS ACID-PROMOTED CATIONIC PI-CYCLIZATIONS OF ALKENYLCYCLOPENTANE-1,3-DIONES AND ALKYNYLCYCLOPENTANE-1,3-DIONES [J].

BALOG, A ;

GEIB, SJ ;

CURRAN, DP .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) :345-352

[7] RING-ENLARGING ANNULATIONS - A ONE-STEP CONVERSION OF CYCLIC SILYL ACYLOINS AND OMEGA-ALKYNYL ACETALS TO POLYCYCLIC ENEDIONES [J].

BALOG, A ;

CURRAN, DP .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) :337-344

[8] ALPHA-KETOCARBONIUM IONS - STEREOCHEMICAL DATA ON HYDRIDE SHIFTS - DETECTION OF A 4-MEMBERED CYCLIC OXONIUM SALT [J].

BEGUE, JP ;

MALISSARD, M .

TETRAHEDRON, 1978, 34 (14) :2095-2103

[9] Ytterbium triflate promoted coupling reaction between aryl alkynes and aldehydes [J].

Curini, M ;

Epifano, F ;

Maltese, F ;

Rosati, O .

SYNLETT, 2003, (04) :552-554

[10] Gold(III) chloride catalyzed domino processes with isobenzopyrylium cation intermediates [J].

Dyker, G ;

Hildebrandt, D ;

Liu, JH ;

Merz, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) :4399-4402

← 1 2 3 4 →