Stereocontrolled Synthesis of Complicated Oxacyclic Compounds via Platinum-Catalyzed [4+2]-Cycloadditions and Annulations of Enynals with Allylic Alcohols

被引：80

作者：

Hsu, Yu-Chia ^{[1
]}

Ting, Chun-Ming ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 06期

关键词：

CYCLOADDITION; CYCLIZATION; GENERATION; ALKENES; IONS;

D O I：

10.1021/ja809560c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report stereoselective synthesis of tricyclic ketals through Pt(II)-catalyzed [4 + 2]-cycloaddition of benzopyrilium/1-en-3-ol functionalities. For nonaromatic enynals, we obtained distinct tricyclic oxacyctic ketones due to occurrence of a new annulation reaction. This work reports the first example that [4 + 2]-cycloadducts are successfully intercepted from such functionalities in diversified approaches. The value of such cycloadditions and annulations are shown by their high diastereoselectivities and chemoselectivities.

引用

收藏

页码：2090 / +

页数：3

相关论文

共 24 条

[1] 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

[2] Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].

Asao, N ;

Kasahara, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506

[3] AuBr3- and Cu(OTf)2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals:: A new synthetic method for functionalized polycyclic hydrocarbons [J].

Asao, N ;

Sato, K ;

Menggenbateer ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3682-3685

[4] Gold- and copper-catalyzed [4+2] benzannulations between enynal or enynone units and 2π-systems [J].

Asao, Naoki .

SYNLETT, 2006, (11) :1645-1656

[5] Synthesis of indoles upon sequential reaction of 3-alkynylpyrrole-2-carboxaldehydes with iodonium ions and alkenes.: Preparation of related benzofuran and benzothiophene derivatives [J].

Barluenga, J ;

Vázquez-Villa, H ;

Ballesteros, A ;

González, JM .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) :526-530

[6] Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes [J].

Barluenga, J ;

Váquez-Villa, H ;

Ballesteros, A ;

González, JM .

ORGANIC LETTERS, 2003, 5 (22) :4121-4123

[7] PtII-catalyzed synthesis of 9-oxabicyclo-[3.3.1]nona-2,6-dienes from 2-alkynyl-1-carbonylbenzenes and allylsilanes by an allylation/annulation cascade [J].

Bhunia, Sabyasachi ;

Wang, Kuo-Chang ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) :5063-5066

[8] ISOLATION AND STRUCTURE ELUCIDATION OF ABRUSLACTONE-A - A NEW OLEANENE-TYPE TRITERPENE FROM THE ROOTS AND VINES OF ABRUS-PRECATORIUS L [J].

CHANG, HM ;

CHIANG, TC ;

MAK, TCW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (20) :1197-1198

[9] 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

[10]

FURSTNER A, 2007, ANGEW CHEM INT EDIT, V46, P4042