Palladium-catalyzed intramolecular chloroamination of alkenes

被引：114

作者：

Michael, Forrest E. ^{[1
]}

Sibbald, Paul A. ^{[1
]}

Cochran, Brian M. ^{[1
]}

机构：

[1] Univ Washington, Dept Chem, Seattle, WA 98195 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 05期

关键词：

D O I：

10.1021/ol702922c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and facile Pd-catalyzed intramolecular chloroamination of unactivated alkenes has been described. This reaction takes place at room temperature and is tolerant of synthetically useful acid-sensitive functional groups. Generally high exo-selectivities are observed in the formation of a variety of 5- and 6-membered rings. This system is unique in its ability to tolerate multidentate ligands on palladium, which opens up the possibility of controlling the absolute sense of induction using a chiral ligand.

引用

页码：793 / 796

页数：4

共 13 条

[1] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES
CARDILLO, G
ORENA, M
[J]. TETRAHEDRON, 1990, 46 (10) : 3321 - 3408
[2] COCHRAN BM, 2008, IN PRESS J AM CHEM S
[3] FeCl2-catalyzed intramolecular chloroamination reactions
Danielec, H
Klügge, J
Schlummer, B
Bach, T
[J]. SYNTHESIS-STUTTGART, 2006, (03): : 551 - 556
[4] Kemp J. E. G., 1991, COMPREHENSIVE ORGANI, V7, P469, DOI DOI 10.1016/B978-0-08-052349-1.00199-2
[5] A novel highly regio- and diastereoselective haloamination of alkenes catalyzed by divalent palladium
Lei, AW
Lu, XY
Liu, GS
[J]. TETRAHEDRON LETTERS, 2004, 45 (08) : 1785 - 1788
[6] Recent development of regio- and stereoselective aminohalogenation reaction of alkenes
Li, Guigen
Kotti, S. R. S. Saibabu
Timmons, Cody
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (17) : 2745 - 2758
[7] Palladium(II)-catalysed intramolecular aminobromination and aminochlorination of olefins
Manzoni, MR
Zabawa, TP
Kasi, D
Chemler, SR
[J]. ORGANOMETALLICS, 2004, 23 (23) : 5618 - 5621
[8] Room temperature palladium-catalyzed intramolecular hydroamination of unactivated alkenes
Michael, FE
Cochran, BM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) : 4246 - 4247
[9] A new class of conformationally rigid analogues of 4-amino-5-halopentanoic acids, potent inactivators of γ-aminobutyric acid aminotransferase
Qiu, J
Silverman, RB
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (04) : 706 - 720
[10] Asymmetric iodolactamization induced by chiral oxazolidine auxiliary
Shen, MH
Li, CZ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) : 7906 - 7909

← 1 2 →