HIGHLY DIASTEREOSELECTIVE HYDROCYANATION OF ALPHA-SULFINYL CYCLOALKANONES

被引：21

作者：

ESCRIBANO, A ^{[1
]}

RUANO, JLG ^{[1
]}

CASTRO, AMM ^{[1
]}

RODRIGUEZ, JH ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM C-1,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON | 1994年 / 50卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)90484-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrocyanation of cyclic alpha-sulfinyl ketones under different conditions has been studied. The obtained results show that compounds derived from cyclohexanone react with Et(2)AlCN yielding only sulfinyl cyanohydrins exhibiting different configurations at sulfur and at hydroxylic carbon. The stereoselectivity is slightly lower but also very high starting from alpha-sulfinyl cyclopentanones. The influence of Lewis acids as well as the stereochemical course of these reactions have also been discussed.

引用

页码：7567 / 7578

页数：12

共 24 条

[1]

Arcamone F., 1981, DOXORUBICIN ANTICANC

[2] PHORBIC ACID, A NEW ACID FROM EUPHORBIUM [J].

BERNATEK, E ;

NORDAL, A ;

OGNER, G .

ACTA CHEMICA SCANDINAVICA, 1963, 17 (09) :2375-&

[3] BIO-ORGANIC SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRINS AND ACYLOINS [J].

BRUSSEE, J ;

ROOS, EC ;

VANDERGEN, A .

TETRAHEDRON LETTERS, 1988, 29 (35) :4485-4488

[4]

BRUSSEE J, 1990, Patent No. 322973

[5] N-METALLO-IMINES - A NEW APPROACH TO ALPHA-AMINO ALCOHOLS FROM CYANOHYDRINS [J].

CAINELLI, G ;

MEZZINA, E ;

PANUNZIO, M .

TETRAHEDRON LETTERS, 1990, 31 (24) :3481-3484

[6] PREPARATION OF 1,2 AMINOLS FROM CYANOHYDRINS VIA N-DIISOBUTYLALUMINIUM IMINES [J].

CAINELLI, G ;

PANUNZIO, M ;

CONTENTO, M ;

GIACOMINI, D ;

MEZZINA, E ;

GIOVAGNOLI, D .

TETRAHEDRON, 1993, 49 (18) :3809-3826

[7] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].

CARRENO, MC ;

RUANO, JLG ;

MARTIN, AM ;

PEDREGAL, C ;

RODRIGUEZ, JH ;

RUBIO, A ;

SANCHEZ, J ;

SOLLADIE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128

[8] SYNTHESIS OF CHIRAL CYCLIC ALPHA-PARA-TOLYLSULFINYL KETONES [J].

CARRENO, MC ;

RUANO, JLG ;

PEDREGAL, C ;

RUBIO, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07) :1335-1337

[9]

EFFENBERGER F, 1991, LIEBIGS ANN CHEM, P269

[10] ENZYME-CATALYZED SYNTHESIS OF (R)-KETONE-CYANOHYDRINS AND THEIR HYDROLYSIS TO (R)-ALPHA-HYDROXY-ALPHA-METHYL-CARBOXYLIC ACIDS [J].

EFFENBERGER, F ;

HORSCH, B ;

WEINGART, F ;

ZIEGLER, T ;

KUHNER, S .

TETRAHEDRON LETTERS, 1991, 32 (23) :2605-2608

← 1 2 3 →