Au(I)-catalyzed cyclization of tert-butyl carbonates derived from homopropargyl alcohols:: A catalytic alternative to cyclic enol carbonates

被引：53

作者：

Kang, JE ^{[1
]}

Shin, S ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

来源：

SYNLETT | 2006年 / 05期

关键词：

gold catalysis; tert-butyl carbonate; homopropargyl alcohol; enol carbonate; ligand;

D O I：

10.1055/s-2006-933110

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Au(I)-complexes catalyze cyclization of tert-butyl carbonates derived from a variety of homopropargyl alcohols. This procedure offers a catalytic alternative to stoichiometric Lewis acids for the preparation of a range of enol carbonates.

引用

页码：717 / 720

页数：4

共 33 条

[1] 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

[2] CARBONATE EXTENSION - A VERSATILE PROCEDURE FOR FUNCTIONALIZATION OF ACYCLIC HOMOALLYLIC ALCOHOLS WITH MODERATE STEREOCONTROL [J].

BARTLETT, PA ;

MEADOWS, JD ;

BROWN, EG ;

MORIMOTO, A ;

JERNSTEDT, KK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (21) :4013-4018

[3] Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies [J].

Bode, JW ;

Carreira, EM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6410-6424

[4] REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF EPOXY ALCOHOLS AND TRIOLS FROM ALLYLIC AND HOMOALLYLIC ALCOHOLS VIA IODO CARBONATES [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4626-4633

[5] New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to oxygen as a surrogate to the aldol reaction [J].

Davies, HML ;

Beckwith, REJ ;

Antoulinakis, EG ;

Jin, QH .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6126-6132

[6] IODINE MONOBROMIDE (IBR) AT LOW-TEMPERATURE - ENHANCED DIASTEREOSELECTIVITY IN ELECTROPHILIC CYCLIZATIONS OF HOMOALLYLIC CARBONATES [J].

DUAN, JJW ;

SMITH, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3703-3711

[7] PHOSPHINE CATALYZED SYNTHESIS OF UNSATURATED CYCLIC CARBONATES FROM CARBON-DIOXIDE AND PROPARGYLIC ALCOHOLS [J].

FOURNIER, J ;

BRUNEAU, C ;

DIXNEUF, PH .

TETRAHEDRON LETTERS, 1989, 30 (30) :3981-3982

[8] Unusual gold(I)-catalyzed isomerization of 3-hydroxylated 1,5-enynes: Highly substrate-dependent reaction manifolds [J].

Gagosz, F .

ORGANIC LETTERS, 2005, 7 (19) :4129-4132

[9] Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction [J].

Gorin, DJ ;

Davis, NR ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11260-11261

[10] Gold catalysis:: Mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects [J].

Hashmi, ASK ;

Weyrauch, JP ;

Frey, W ;

Bats, JW .

ORGANIC LETTERS, 2004, 6 (23) :4391-4394

← 1 2 3 4 →