A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines

被引：113

作者：

Alcaide, B ^{[1
]}

Almendros, P

Alonso, JM

Aly, MF

机构：

[1] Univ Complutense Madrid, Dept Quim Organ 1, Fac Ciencias Quim, Madrid 28040, Spain

[2] S Valley Univ, Fac Sci Qena, Dept Chem, Qena, Egypt

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 23期

关键词：

D O I：

10.1021/ol0167412

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first examples accounting for the catalytic deprotection of allylic amines by using reagents different from palladium catalysts have been achieved via Grubbs' carbene-mediated reaction. The current mechanistic hypothesis invokes a nitrogen-assisted ruthenium-catalyzed isomerization, followed by hydrolysis of the enamine intermediate. We believe that an unprecedented mode of ring opening of the ruthena-cyclobutane was involved.

引用

页码：3781 / 3784

页数：4

共 25 条

[1] 4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis [J].

Alcaide, B ;

Almendros, P .

CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :226-240

[2] Recent progress in the synthesis and reactivity of azetidine-2,3-diones. A review [J].

Alcaide, B ;

Almendros, P .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2001, 33 (04) :315-+

[3]

Alcaide B, 2001, SYNLETT, P1531

[4]

Alcaide B, 2001, SYNLETT, P773

[5]

ALCAIDE B, UNPUB

[6]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[7] Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene. [J].

Badorrey, R ;

Cativiela, C ;

Díaz-de-Villegas, MD ;

Gálvez, JA .

TETRAHEDRON, 1999, 55 (24) :7601-7612

[8] Homogeneous metathesis polymerization by well-defined group VI and group VIII transition-metal alkylidenes: Fundamentals and applications in the preparation of advanced materials [J].

Buchmeiser, MR .

CHEMICAL REVIEWS, 2000, 100 (04) :1565-1604

[9] Unusual molybdenum mediated C-N bond activation [J].

Cameron, TM ;

Abboud, KA ;

Boncella, JM .

CHEMICAL COMMUNICATIONS, 2001, (13) :1224-+

[10]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

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