ACYCLIC STEREOCONTROL IN THE ADDITION OF TRIMETHYLSILYL CYANIDE TO N-SUBSTITUTED IMINES OF (2S)-LACTIC ALDEHYDE

被引：33

作者：

CAINELLI, G ^{[1
]}

GIACOMINI, D ^{[1
]}

TRERE, A ^{[1
]}

GALLETTI, P ^{[1
]}

机构：

[1] UNIV BOLOGNA, DIPARTIMENTO CHIM G CIAMICIAN, I-40126 BOLOGNA, ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 07期

关键词：

D O I：

10.1016/0957-4166(95)00203-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The cyanosilylation of a series of N-substituted lactaldehyde imines is reported. The trimethylsilylcyanide addition affords optically active alpha-amino nitriles. All the imines show a syn diastereofacial selectivity that is maintained irrespective to the nature of the Lewis acid employed and even remains in the noncatalyzed reaction.

引用

页码：1593 / 1600

页数：8

共 18 条

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

CAINELLI, G ;

GIACOMINI, D ;

MEZZINA, E ;

PANUNZIO, M ;

ZARANTONELLO, P .

TETRAHEDRON LETTERS, 1991, 32 (25) :2967-2970

[2] REVERSAL OF DIASTEREOSELECTIVITY IN THE ADDITION OF C-NUCLEOPHILES TO N-TRIMETHYLSILYL IMINES VIA GRIGNARD DERIVED ORGANO COPPER-BORON TRIFLUORIDE REAGENTS [J].

CAINELLI, G ;

GIACOMINI, D ;

PANUNZIO, M ;

ZARANTONELLO, P .

TETRAHEDRON LETTERS, 1992, 33 (50) :7783-7786

[3] 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

[4] BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF (+)-PS-5 [J].

CAINELLI, G ;

PANUNZIO, M ;

GIACOMINI, D ;

MARTELLI, G ;

SPUNTA, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6879-6880

[5] DIASTEREOSELECTIVE STRECKER SYNTHESIS USING ALPHA-PHENYLGLYCINOL AS CHIRAL AUXILIARY [J].

CHAKRABORTY, TK ;

REDDY, GV ;

HUSSAIN, KA .

TETRAHEDRON LETTERS, 1991, 32 (51) :7597-7600

[6] UNIQUE STEREOCONTROL IN EUROPIUM (III)-CATALYZED CYANOSILYLATION OF CHIRAL ALPHA-ALKOXY AND ALPHA-AMINO ALDEHYDES [J].

GU, JH ;

OKAMOTO, M ;

TERADA, M ;

MIKAMI, K ;

NAKAI, T .

CHEMISTRY LETTERS, 1992, (07) :1169-1172

[7] STUDIES ON THE SYNTHESIS OF CYANOMETHYLENEAMINO PSEUDOPEPTIDES [J].

HERRANZ, R ;

SUAREZGEA, ML ;

VINUESA, S ;

GARCIALOPEZ, MT .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5186-5191

[8] ENANTIOSELECTIVE ADDITION-REACTION OF TRIMETHYLSILYL CYANIDE WITH ALDEHYDES USING A CHIRAL TIN(II) LEWIS ACID [J].

KOBAYASHI, S ;

TSUCHIYA, Y ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1991, (04) :541-544

[9] A FACILE SYNTHESIS OF CYANOHYDRIN TRIMETHYLSILYL ETHERS BY THE ADDITION-REACTION OF TRIMETHYLSILYL CYANIDE WITH ALDEHYDES UNDER BASIC CONDITION [J].

KOBAYASHI, S ;

TSUCHIYA, Y ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1991, (04) :537-540

[10] SYNTHESIS OF ALPHA-AMINONITRILES BY SELF-CATALYZED, STOICHIOMETRIC REACTION OF PRIMARY AMINES, ALDEHYDES, AND TRIMETHYLSILYL CYANIDE [J].

LEBLANC, JP ;

GIBSON, HW .

TETRAHEDRON LETTERS, 1992, 33 (42) :6295-6298

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