Ketone synthesis by intramolecular acylation of organorhodium(I) with ester

被引:126
作者
Miura, T [1 ]
Sasaki, T [1 ]
Nakazawa, H [1 ]
Murakami, M [1 ]
机构
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
关键词
D O I
10.1021/ja043123i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New cyclization reactions forming cyclic ketones were developed wherein an intermediate organorhodium(I) species underwent intramolecular acylation with an ester group. A 2-norbornanone skeleton is constructed in a single operation through successive multiple carbon-carbon bond formation. The reactions ended up with generation of an alkoxyrhodium(I) species to promote the next catalytic cycle. Copyright © 2005 American Chemical Society.
引用
收藏
页码:1390 / 1391
页数:2
相关论文
共 24 条
[1]   Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
ORGANIC LETTERS, 1999, 1 (10) :1683-1686
[2]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[3]   Rhodium catalysed addition of boronic acids to anhydrides: a new method for the synthesis of ketones [J].
Frost, CG ;
Wadsworth, KJ .
CHEMICAL COMMUNICATIONS, 2001, (22) :2316-2317
[4]  
Fürstner A, 2001, ADV SYNTH CATAL, V343, P343
[5]   Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates [J].
Hayashi, T ;
Takahashi, M ;
Takaya, Y ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5052-5058
[6]   Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].
Hayashi, T ;
Inoue, K ;
Taniguchi, N ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919
[7]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[8]   N-BOC-L-valine-connected amidomonophosphane rhodium(I) catalyst for asymmetric arylation of N-tosylarylimines with arylboroxines [J].
Kuriyama, M ;
Soeta, T ;
Hao, XY ;
Chen, O ;
Tomioka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8128-8129
[9]   Regioselective rhodium-catalyzed addition of arylboronic acids to alkynes with a pyridine-substituted water-soluble ligand [J].
Lautens, M ;
Yoshida, M .
ORGANIC LETTERS, 2002, 4 (01) :123-125
[10]   Rhodium-catalyzed addition/ring-opening reaction of arylboronic acids with cyclobutanones [J].
Matsuda, T ;
Makino, M ;
Murakami, M .
ORGANIC LETTERS, 2004, 6 (08) :1257-1259