ADDITION OF GRIGNARD AND ORGANOLITHIUM REAGENTS TO N-SULFONYL ALDIMINES GENERATED INSITU FROM ALDEHYDES AND N-SULFINYL SULFONAMIDES

被引：99

作者：

SISKO, J ^{[1
]}

WEINREB, SM ^{[1
]}

机构：

[1] PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 01期

关键词：

D O I：

10.1021/jo00288a080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of organometallic reagents to imines is often a poor synthetic reaction due to competing processes such as a-deprotonation and reductive dimerization. Alkyl and aryl Grignard and organolithium species have proven particularly troublesome, although some useful solutions to the problem have recently been presented1-4. © 1990, American Chemical Society. All rights reserved.

引用

收藏

页码：393 / 395

页数：3

相关论文

共 25 条

[1] HETEROCYCLEN DURCH DIENSYNTHESE .2. N-[BUTYLOXYCARBONYLMENTHYLEN]-P-TOLUOLSULFONAMID EIN NEUES DIENOPHIL ZUR DARSTELLUNG VON PYRIDIN- PIPERIDEIN- UND PIPERIDIN-DERIVATEN DURCH DIELS-ALDER-SYNTHESE [J].

ALBRECHT, R ;

KRESZE, G .

CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05) :1431-&

[2] ARYLSULFONYLIMINE - DARSTELLUNG EIGENSCHAFTEN UND REAKTIVITAT [J].

ALBRECHT, R ;

KRESZE, G ;

MLAKAR, B .

CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (02) :483-&

[3] THE ACTIVATION OF IMINES TO NUCLEOPHILIC-ATTACK BY GRIGNARD-REAGENTS [J].

BROOK, MA ;

JAHANGIR .

SYNTHETIC COMMUNICATIONS, 1988, 18 (09) :893-898

[4] ORGANOLITHIUM ADDITION TO ALDEHYDE DIMETHYLHYDRAZONES - A HIGHLY DIASTEREOCONTROLLED SYNTHESIS OF THREO 2-AMINO ALCOHOLS AND (1R,2R)-(-)-NORPSEUDOEPHEDRINE [J].

CLAREMON, DA ;

LUMMA, PK ;

PHILLIPS, BT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8265-8266

[5] DIASTEREOSELECTIVE ADDITION OF LITHIATED N,N-DIETHYL-ORTHO-TOLUAMIDE TO CHIRAL ISOPROPYLIDINE GLYCERALDEHYDE IMINES - ASYMMETRIC-SYNTHESIS OF 3-SUBSTITUTED 3,4-DIHYDRO-1(2H)-ISOQUINOLONES [J].

CLARK, RD ;

JAHANGIR ;

SOUCHET, M ;

KERN, JR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) :930-931

[6] A NEW SYNTHESIS OF PRIMARY AMINES FROM DIARYLIDENESULFAMIDES [J].

DAVIS, FA ;

GIANGIORDANO, MA ;

STARNER, WE .

TETRAHEDRON LETTERS, 1986, 27 (34) :3957-3960

[7] ORGANOCERIUM ADDITIONS TO SAMP-HYDRAZONES - GENERAL-SYNTHESIS OF CHIRAL AMINES [J].

DENMARK, SE ;

WEBER, T ;

PIOTROWSKI, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2224-2225

[8] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED PRIMARY AMINES BY NUCLEOPHILIC-ADDITION TO ALDEHYDE-SAMP HYDRAZONES [J].

ENDERS, D ;

SCHUBERT, H ;

NUBLING, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (12) :1109-1110

[9] ALLYLIC DEUTERATION AND TRITIATION OF OLEFINS WITH N-SULFINYLSULFONAMIDES [J].

HORI, T ;

SINGER, SP ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (07) :1456-1459

[10]

KECK GE, 1985, J ORG CHEM, V50, P147