Highly stereoselective syntheses of five- and seven-membered ring heterocycles from ylides generated by catalytic reactions of styryldiazoacetates with aldehydes and imines

被引：55

作者：

Doyle, MP ^{[1
]}

Hu, WH ^{[1
]}

Timmons, DJ ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 23期

关键词：

D O I：

10.1021/ol016703i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Styryldiazoacetates are effective reactants for ylide formation that results in the formation of dilhydropyrroles and dihydroazepines with high stereocontrol and high yields.

引用

页码：3741 / 3744

页数：4

共 24 条

[1] TRANSITION-METAL-CATALYZED DECOMPOSITION OF DIAZO(TRIALKYLSILYL)-ACETATES - INTERMOLECULAR FORMATION AND TRAPPING OF CARBONYL YLIDES
ALT, M
MAAS, G
[J]. TETRAHEDRON, 1994, 50 (25) : 7435 - 7444
[2] Anac O, 1997, LIEBIGS ANN-RECL, P1249
[3] [Anonymous], 1997, Organic Reactions
[4] 1,7-electrocyclisation of non-stabilised α,β:γ,δ-unsaturated azomethine ylides
Arany, A
Bendell, D
Groundwater, PW
Garnett, I
Nyerges, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (18): : 2605 - 2608
[5] Nonstabilized N-unsubstituted azomethine ylides:: A synthesis of indolizidine 239CD
Clark, RB
Pearson, WH
[J]. ORGANIC LETTERS, 1999, 1 (02) : 349 - 351
[6] Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid
Davies, HML
Bruzinski, PR
Lake, DH
Kong, N
Fall, MJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) : 6897 - 6907
[7] CARBONYL YLIDES FROM ALDEHYDES AND CARBENES
DEMARCH, P
HUISGEN, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) : 4952 - 4952
[8] Doyle M. P., 1998, MODERN CATALYTIC MET
[9] Epoxides and aziridines from diazoacetates via ylide intermediates
Doyle, MP
Hu, WH
Timmons, DJ
[J]. ORGANIC LETTERS, 2001, 3 (06) : 933 - 935
[10] Stereocontrol in intermolecular dirhodium(II)-catalyzed carbonyl ylide formation and reactions. Dioxolanes and dihydrofurans
Doyle, MP
Forbes, DC
Protopopova, MN
Stanley, SA
Vasbinder, MM
Xavier, KR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7210 - 7215

← 1 2 3 →