Unusual selectivity of unprotected aziridines in palladium-catalyzed allylic amination enables facile preparation of branched aziridines

被引：69

作者：

Watson, IDG ^{[1
]}

Styler, SA ^{[1
]}

Yudin, AK ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 16期

关键词：

D O I：

10.1021/ja049242f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Functionalized branched aziridines can be prepared in high yields and with high levels of regioselectivity using unprotected aziridines as nitrogen sources in palladium-catalyzed allylic amination. High levels of enantioselectivity can be achieved with BINAP on palladium. This methodology allows for strategic placement of an aziridine-containing fragment within a complex molecule environment for further elaboration. Copyright © 2003 American Chemical Society.

引用

页码：5086 / 5087

页数：2

共 32 条

[1]

AKERMARK B, 1985, ORGANOMETALLICS, V4, P1275

[2]

Alezra V, 2001, EUR J ORG CHEM, V2001, P2589

[3] Fast ester cleavage of sterically hindered α- and β-aminoesters under non-aqueous conditions.: Application to the kinetic resolution of aziridine esters [J].

Alezra, V ;

Bouchet, C ;

Micouin, L ;

Bonin, M ;

Husson, HP .

TETRAHEDRON LETTERS, 2000, 41 (05) :655-658

[4] ASYMMETRIC SYNTHESES OF OPTICALLY-ACTIVE ALPHA,BETA-DISUBSTITUTED BETA-AMINO ACIDS [J].

BURGESS, K ;

LIU, LT ;

PAL, B .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4758-4763

[5]

Cardillo G, 2003, ALDRICHIM ACTA, V36, P39

[6] ASYMMETRIC ALLYLIC AMINATION CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEXES [J].

HAYASHI, T ;

KISHI, K ;

YAMAMOTO, A ;

ITO, Y .

TETRAHEDRON LETTERS, 1990, 31 (12) :1743-1746

[7] PREPARATION OF N-DIPROTECTED ALLYLIC AMINES VIA PALLADIUM(0)-CATALYZED COUPLING REACTIONS [J].

HUTCHINS, RO ;

WEI, J ;

RAO, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :4007-4009

[8] Stereoselective allyl amine synthesis via enantioselective addition of diethylzinc and sigmatropic rearrangement; Synthesis of lentiginosine [J].

Ichikawa, Y ;

Ito, T ;

Nishiyama, T ;

Isobe, M .

SYNLETT, 2003, (07) :1034-1036

[9] Asymmetric intramolecular allylic amination: Straightforward approach to chiral C1-substituted tetrahydroisoquinolines [J].

Ito, K ;

Akashi, S ;

Saito, B ;

Katsuki, T .

SYNLETT, 2003, (12) :1809-1812

[10] Allylic amination [J].

Johannsen, M ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (04) :1689-1708

← 1 2 3 4 →