Copper-catalyzed tandem conjugate addition-electrophilic trapping: Ketones, esters, and nitriles as terminal electrophiles

被引：112

作者：

Agapiou, K ^{[1
]}

Cauble, DF ^{[1
]}

Krische, MJ ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 14期

关键词：

D O I：

10.1021/ja030603l

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Exposure of enone substrates 1a?18a, which possess appendant ketone, ester, and nitrile moieties, to Et2Zn in the presence of catalytic Cu(OTf)2/P(OEt)3 provides the cyclized products in good to excellent yields and diastereoselectivities. These results represent the first use of ketones, esters, and nitriles as terminal electrophiles in Cu-catalyzed conjugate addition?electrophilic trapping. Copyright © 2004 American Chemical Society.

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页码：4528 / 4529

页数：2

相关论文

共 32 条

[1] Catalytic crossed Michael cycloisomerization of thioenoates:: Total synthesis of (±)-ricciocarpin A [J].

Agapiou, K ;

Krische, MJ .

ORGANIC LETTERS, 2003, 5 (10) :1737-1740

[2] Tandem enantioselective conjugate addition: Electrophile trapping reactions. application in the formation of syn or anti aldols [J].

Alexakis, A ;

Trevitt, GP ;

Bernardinelli, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4358-4359

[3]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[4] Catalytic enantioselective synthesis of (-)-prostaglandin E1 methyl ester based on a tandem 1,4-addition-aldol reaction [J].

Arnold, LA ;

Naasz, R ;

Minnaard, AJ ;

Feringa, BL .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7244-7254

[5] Catalytic enantioselective synthesis of prostaglandin E1 methyl ester using a tandem 1,4-addition-aldol reaction to a cyclopenten-3,5-dione monoacetal [J].

Arnold, LA ;

Naasz, R ;

Minnaard, AJ ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) :5841-5842

[6] Diastereoselective cobalt-catalyzed aldol and Michael cycloreductions [J].

Baik, TG ;

Luis, AL ;

Wang, LC ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) :5112-5113

[7]

Blaise EE, 1901, CR HEBD ACAD SCI, V132, P478

[8] Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization [J].

Cauble, DF ;

Gipson, JD ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1110-1111

[9]

Chapdelaine M.J., 1990, ORG REACT, V38, P225

[10] Efficient cu-catalyzed asymmetric conjugate additions of alkylzincs to trisubstituted cyclic enones [J].

Degrado, SJ ;

Mizutani, H ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13362-13363

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