Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds

被引:26
作者
Burtoloso, Antonio C. B. [1 ]
Santiago, Joao V. [1 ]
Bernardim, Barbara [1 ]
Talero, Alexander G. [1 ]
机构
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Asymmetric catalysis; carbenes; diazocarbonyls; enantioselective; insertion reactions; metal catalysis; DIAZO-COMPOUNDS; DIRHODIUM(II) CARBOXYLATES; ASYMMETRIC-SYNTHESIS; 3-COMPONENT REACTION; CARBENOID INSERTION; EFFICIENT APPROACH; BONDS; DIAZOACETATES; RHODIUM; DIAZOKETONES;
D O I
10.2174/157017941205150821153658
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Insertion of diazocarbonyl-derived metallocarbenes into X-H bonds (X= H, C, Si, N, O, S, P, Se) has proven to be a very important method for the construction of C-X bonds in organic chemistry. This mini-review provides a brief historical background, mechanistic aspects and a summary of recent breakthroughs in the area of enantioselective metal-catalyzed N-H and O-H insertion reactions.
引用
收藏
页码:650 / 659
页数:10
相关论文
共 55 条
[2]   CpRu-Catalyzed O-H Insertion and Condensation Reactions of α-Diazocarbonyl Compounds [J].
Austeri, Martina ;
Rix, Diane ;
Zeghida, Walid ;
Lacour, Jerome .
ORGANIC LETTERS, 2011, 13 (06) :1394-1397
[3]   Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen- or sulfur-containing nucleophilic substrates: Synthetic uses and mechanistic insights [J].
Aviv, Iris ;
Gross, Zeev .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (13) :3995-4005
[4]   Cu(I)-carbenoid- and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of α-diazo compounds into N-H bonds [J].
Bachmann, S ;
Fielenbach, D ;
Jorgensen, KA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (20) :3044-3049
[5]   REACTION OF N-DISUBSTITUTED GLYCYL CHLORIDES WITH DIAZOMETHANE - A NEW SYNTHESIS OF SOME BETA-ALANINE DERIVATIVES - AMINO ACIDS .5. [J].
BALENOVIC, K ;
BREGANT, N ;
CERAR, D ;
TKALCIC, M .
JOURNAL OF ORGANIC CHEMISTRY, 1951, 16 (08) :1308-1310
[6]   Rh(II)-Catalyzed Reactions of Differentially Substituted Bis(diazo) Functionalities [J].
Bonderoff, Sara A. ;
Padwa, Albert .
ORGANIC LETTERS, 2013, 15 (16) :4114-4117
[7]   A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds [J].
Bulugahapitiya, P ;
Landais, Y ;
ParraRapado, L ;
Planchenault, D ;
Weber, V .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1630-1641
[8]  
CAMA LD, 1978, TETRAHEDRON LETT, P4233
[9]   *17-ISO-ALLOPREGNAN - STEROIDE .1. [J].
CASANOVA, R ;
REICHSTEIN, T .
HELVETICA CHIMICA ACTA, 1949, 32 (03) :647-656
[10]   METHOXYKETONE AUS DIAZOKETONEN .5. STEROIDE [J].
CASANOVA, R ;
REICHSTEIN, T .
HELVETICA CHIMICA ACTA, 1950, 33 (02) :417-422