γ-methylidene-δ-valerolactones as a coupling partner for cycloaddition:: Palladium-catalyzed [4+3] cycloaddition with nitrones

被引：161

作者：

Shintani, Ryo ^{[1
]}

Murakami, Masataka ^{[1
]}

Hayashi, Tamio ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 41期

关键词：

D O I：

10.1021/ja073997f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new type of reagent, gamma-methylidene-delta-valerolactones, has been devised, which acts as a four-carbon unit in a palladium-catalyzed cycloaddition reaction through the formation of a 1,4-zwitterionic species. The utility has been demonstrated in the context of stereoselective [4 + 3] cycloaddition with nitrones to provide highly functionalized 1,2-oxazepines, including the asymmetric variant with high enantioselectivity.

引用

页码：12356 / +

页数：3

共 35 条

[1] Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects
Arnold, LA
Imbos, R
Mandoli, A
de Vries, AHM
Naasz, R
Feringa, BL
[J]. TETRAHEDRON, 2000, 56 (18) : 2865 - 2878
[2] The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings
Battiste, MA
Pelphrey, PM
Wrightthl, DL
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (13) : 3438 - 3447
[3] Asymmetric allylic alkylation of ketone enolates: An asymmetric claisen surrogate
Burger, EC
Tunge, JA
[J]. ORGANIC LETTERS, 2004, 6 (22) : 4113 - 4115
[4] Highly stereoselective formal [3+3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes
Chan, Audrey
Scheidt, Karl A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) : 5334 - +
[5] Chan DMT, 2002, CYCLOADDITION REACTIONS IN ORGANIC SYNTHESIS, P57
[6] SYNTHESES BY MEANS OF 1-ALKYLIDENE- AND 1-(ARYLALKYLIDENE)-3-PYRAZOLIDONE N,N-BETAINES A NEW TYPE OF STABLE AZOMETHINE IMINE
DORN, H
OTTO, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (03) : 214 - &
[7] REACTION OF PYRAZOLID-3-ONE WITH CARBONYL COMPOUNDS
DORN, H
OTTO, A
[J]. CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (09): : 3287 - &
[8] Ligand-induced acceleration of the intramolecular [3+2] cycloaddition between alkynes and alkylidenecyclopropanes
Durán, J
Gulías, M
Castedo, L
Mascareñas, JL
[J]. ORGANIC LETTERS, 2005, 7 (25) : 5693 - 5696
[9] Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents
Feringa, BL
Pineschi, M
Arnold, LA
Imbos, R
de Vries, AHM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) : 2620 - 2623
[10] Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition
Feringa, BL
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 346 - 353

← 1 2 3 4 →