Site- and enantiocontrol in intramolecular C-H insertion reactions of alpha-diazo carbonyl compounds catalyzed by dirhodium(II) carboxylates

被引：41

作者：

Hashimoto, S ^{[1
]}

Watanabe, N ^{[1
]}

Anada, M ^{[1
]}

Ikegami, S ^{[1
]}

机构：

[1] TEIKYO UNIV, FAC PHARMACEUT SCI, SAGAMIKO, KANAGAWA 19901, JAPAN

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 1996年 / 54卷 / 11期

关键词：

D O I：

10.5059/yukigoseikyokaishi.54.988

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The full potential of rhodium(II)-catalyzed intramolecular C-H insertion reactions of alpha-diazo carbonyl compounds as a powerful tool for the construction of both carbocycles and heterocycles has been developed by variation of the bridging ligands of the dirhodium(II) catalysts: (1) Dirhodium(II) tetrakis(triphenylacetate) featured by the steric bulk of the bridging ligands on the rhodium has been demonstrated to exhibit an exceptionally high order of selectivity for C-H insertion into methylene over methine on a cycloalkane ring as well as for aromatic substitution over aliphatic C-H insertion. (2) Dirhodium(II) complexes incorporating N-phthaloyl-(S)-amino acids as bridging ligands have proven to be the chiral catalysts of choice for allowing high levels of differentiation of enantiotopic methylene C-H bonds and enantiotopic benzene rings, affording optically active cyclopentanone, 2-azetidinone, and 2-indanone derivatives in up to 80%, 96%, and 98% ee, respectively.

引用

页码：988 / 999

页数：12

共 54 条

[11] ELECTROPHILIC METAL CARBENES AS REACTION INTERMEDIATES IN CATALYTIC REACTIONS [J].

DOYLE, MP .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :348-356

[12] CONSTRUCTION OF BETA-LACTAMS BY HIGHLY SELECTIVE INTRAMOLECULAR C-H INSERTION FROM RHODIUM(II) CARBOXYLATE CATALYZED-REACTIONS OF DIAZOACETAMIDES [J].

DOYLE, MP ;

SHANKLIN, MS ;

OON, SM ;

PHO, HQ ;

VANDERHEIDE, FR ;

VEAL, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3384-3386

[13] CONFORMATIONAL AND ELECTRONIC PREFERENCES IN RHODIUM(II) CARBOXYLATE AND RHODIUM(II) CARBOXAMIDE CATALYZED CARBON-HYDROGEN INSERTION REACTIONS OF N,N-DISUBSTITUTED DIAZOACETOACETAMIDES [J].

DOYLE, MP ;

TAUNTON, J ;

PHO, HQ .

TETRAHEDRON LETTERS, 1989, 30 (40) :5397-5400

[14]

Doyle MP, 1996, ALDRICHIM ACTA, V29, P3

[15]

DOYLE MP, 1991, RECL TRAV CHIM PAY B, V110, P305

[16] RHODIUM(II) ACETATE AND NAFION-H CATALYZED DECOMPOSITION OF N-ARYLDIAZOAMIDES - AN EFFICIENT SYNTHESIS OF 2(3H)-INDOLINONES [J].

DOYLE, MP ;

SHANKLIN, MS ;

PHO, HQ ;

MAHAPATRO, SN .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1017-1022

[17] ELECTRONIC AND STERIC CONTROL IN CARBON HYDROGEN INSERTION REACTIONS OF DIAZOACETOACETATES CATALYZED BY DIRHODIUM(II) CARBOXYLATES AND CARBOXAMIDES [J].

DOYLE, MP ;

WESTRUM, LJ ;

WOLTHUIS, WNE ;

SEE, MM ;

BOONE, WP ;

BAGHERI, V ;

PEARSON, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :958-964

[18] THE CHEMISTRY, STRUCTURE, AND METAL METAL-BONDING IN COMPOUNDS OF RHODIUM(II) [J].

FELTHOUSE, TR .

PROGRESS IN INORGANIC CHEMISTRY, 1982, 29 :73-166

[19] CHIRAL SYNTHESIS OF ISOCARBACYCLIN ((+)-9(0)-METHANO-DELTA-6(9-ALPHA)-PGI1) INTERMEDIATE VIA RHODIUM(II)-CATALYZED INTRAMOLECULAR C-H INSERTION REACTION [J].

HASHIMOTO, S ;

SHINODA, T ;

SHIMADA, Y ;

HONDA, T ;

IKEGAMI, S .

TETRAHEDRON LETTERS, 1987, 28 (06) :637-640

[20] HIGHLY SELECTIVE INSERTION INTO AROMATIC C-H BONDS IN RHODIUM(II) TRIPHENYLACETATE-CATALYZED DECOMPOSITION OF ALPHA-DIAZOCARBONYL COMPOUNDS [J].

HASHIMOTO, S ;

WATANABE, N ;

IKEGAMI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (20) :1508-1510

← 1 2 3 4 5 6 →