A two-carbon homologation of aldehydes and ketones using ynamides

被引：53

作者：

You, Lingfeng

Al-Rashid, Ziyad F.

Figueroa, Ruth

Ghosh, Sunil K.

Li, Gang

Lu, Ting

Hsung, Richard P.

机构：

[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA

[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA

来源：

SYNLETT | 2007年 / 11期

关键词：

two-carbon hornologation; ynamide; torquoselective ring opening; oxetene; E-acrylic amides;

D O I：

10.1055/s-2007-984513

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of ynamides with Lewis acid activated aldehydes, enals, or ketones in the formation of acrylic amides are described here. The overall process is an equivalent of a two-carbon homologation of aldehydes or ketones and is selective for the E-isomer.

引用

收藏

页码：1656 / 1662

页数：7

相关论文

共 42 条

[1] Regiocontrolled carbometallation reactions of ynamides [J].

Chechik-Lankin, H ;

Livshin, S ;

Marek, I .

SYNLETT, 2005, (13) :2098-2100

[2] Palladium-catalyzed Suzuki-Miyaura coupling reactions involving β,β-dihaloenamides:: Application to the synthesis of disubstituted ynamides [J].

Couty, S ;

Barbazanges, M ;

Meyer, C ;

Cossy, J .

SYNLETT, 2005, (06) :905-910

[3] Diastereoselective gold-catalyzed cycloisomerizations of ene-ynamides [J].

Couty, Sylvain ;

Meyer, Christophe ;

Cossy, Janine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6726-6730

[4] Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions [J].

Dolbier, WR ;

Koroniak, H ;

Houk, KN ;

Sheu, CM .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (10) :471-477

[5] Synthesis of highly substituted indolines and indoles via intramolecular [4+2] cycloaddition of ynamides and conjugated enynes [J].

Dunetz, JR ;

Danheiser, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5776-5777

[6] Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides [J].

Dunetz, JR ;

Danheiser, RL .

ORGANIC LETTERS, 2003, 5 (21) :4011-4014

[7] Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement [J].

Engel, Douglas A. ;

Dudley, Gregory B. .

ORGANIC LETTERS, 2006, 8 (18) :4027-4029

[8] A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides [J].

Frederick, MO ;

Mulder, JA ;

Tracey, MR ;

Hsung, RP ;

Huang, J ;

Kurtz, KCM ;

Shen, LC ;

Douglas, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2368-2369

[9]

FUKS R, 1970, CHEM BER-RECL, V103, P564

[10]

HASEGAWA M, 2007, IN PRESS J ORG CHEM, P72

← 1 2 3 4 5 →