Rh-catalyzed π-facial selective intermolecular hydroacylation of norbornenes

被引：49

作者：

Tanaka, K ^{[1
]}

Tanaka, M ^{[1
]}

Suemune, H ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, Fukuoka 8128582, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 36期

基金：

日本学术振兴会;

关键词：

Rh-complex; hydroacylation; norbornene; pi-facial selection; C-C forming reaction; C-H activation;

D O I：

10.1016/j.tetlet.2005.07.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh-catalyzed pi-facial selective intermolecular hydroacylations of norbornenes with salicylaldehyde have been attained. In the reaction with norbornylene, the exo-hydroacylated product was produced because of steric hindrance. In the case of norbornadiene, the endo-product was obtained because of chelation effect. Lastly, because of chelation and remote substituent effects, the product formed in the reaction of 7-tert-butoxynorbornadiene was the endo,syn-product. Deuterium-labeling experiments revealed that the hydroacylation stereoselectively proceeded via endo- and exo-intermediates. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6053 / 6056

页数：4

共 43 条

[1] Synthesis of cyclooctenones using intramolecular hydroacylation [J].

Aloise, AD ;

Layton, ME ;

Shair, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (50) :12610-12611

[2] Advances and adventures in amination reactions of olefins and alkynes [J].

Beller, M ;

Breindl, C ;

Eichberger, M ;

Hartung, CG ;

Seayad, J ;

Thiel, OR ;

Tillack, A ;

Trauthwein, H .

SYNLETT, 2002, (10) :1579-1594

[3]

Breit B, 2001, SYNTHESIS-STUTTGART, P1

[4] HOMOGENEOUS HYDROFORMYLATION OF ALKENES WITH HYDRIDOCARBONYLTRIS-(TRIPHENYLPHOSPHINE)RHODIUM(I) AS CATALYST [J].

BROWN, CK ;

WILKINSON, G .

JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1970, (17) :2753-+

[5]

BROWN CK, 1969, TETRAHEDRON LETT, P1725

[6] RHODIUM-CATALYZED HYDROAMINATION-HYDROARYLATION OF NORBORNENE WITH ANILINE, TOLUIDINES OR DIPHENYLAMINE [J].

BRUNET, JJ ;

COMMENGES, G ;

NEIBECKER, D ;

PHILIPPOT, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 469 (02) :221-228

[7]

*CCDC, CCDC260662

[8]

*CCDC, 260664 CCDC

[9]

*CCDC, 260663 CCDC

[10] Inductive and resonance effects of substituents on π-face selection [J].

Cieplak, AS .

CHEMICAL REVIEWS, 1999, 99 (05) :1265-1336

← 1 2 3 4 5 →