STEREOSELECTIVE VINYLATION OF AMINO ALDEHYDES USING 2-TRIMETHYLSILYLETHYLIDENTRIPHENYLPHOSPHORANE

被引：23

作者：

FRANCIOTTI, M

MANN, A

TADDEI, M

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN UGO SCHIFF,VIA G CAPPONI 9,I-50121 FLORENCE,ITALY

[2] CNRS,CTR NEUROCHIM,PHARMACOCHIM MOLEC LAB,F-67084 STRASBOURG,FRANCE

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)93602-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Trimethylsilylethylidentriphenylphosphorane reacts stereoselectively with alpha-amino aldehydes giving the Cram chelation controlled product of vinylation of the carbonyl group. The olefinic 1,2-amino alcohols obtained with this reaction are important intermediates for the preparation of peptides analogues and they were employed for the preparation of N-Boc-statine.

引用

收藏

页码：6783 / 6786

页数：4

相关论文

共 22 条

[1]

AMBASHT S, 1980, SYNTHESIS-STUTTGART, P318

[2] OXAZOLIDIN-2-ONES FROM ALLYLIC AMINES BY MEANS OF IODINE AND CARBONATE ANION ON POLYMERIC SUPPORT - A CONVENIENT SYNTHESIS OF (+/-)-PROPRANOLOL [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :713-717

[3]

FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676

[4]

FLEMING I, 1979, SYNTHESIS-STUTTGART, P446

[5] 2-OXAZOLIDONE FORMATION BY PYROLYSIS OF BETA-IODOCARBAMATES . A STEREOSELECTIVE REACTION [J].

FOGLIA, TA ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1680-&

[6] AN ASYMMETRIC-SYNTHESIS OF 5-O-CARBAMOYLPOLYOXAMIC ACID FROM D-SERINE [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :2979-2984

[7] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

[8] SYNTHESIS OF NEW DIPEPTIDE ANALOGS CONTAINING NOVEL KETOVINYL AND HYDROXYETHYLIDENE ISOSTERES VIA GRIGNARD ADDITION TO CHIRAL ALPHA-AMINO ALDEHYDES [J].

HANSON, GJ ;

LINDBERG, T .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5399-5401

[9] SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND D-THREO-SPHINGOSINE DERIVATIVES FROM L-SERINE [J].

HEROLD, P .

HELVETICA CHIMICA ACTA, 1988, 71 (02) :354-362

[10] [2-(TRIMETHYLSILYL)ETHYLIDENE]TRIS(2-METHYLPHENYL)PHOSPHORANE, A MODIFIED SEYFERTH-WITTIG REAGENT FOR THE STEREOSELECTIVE SYNTHESES OF Z-ALLYLTRIMETHYLSILANES [J].

IIO, H ;

ISHII, M ;

TSUKAMOTO, M ;

TOKOROYAMA, T .

TETRAHEDRON LETTERS, 1988, 29 (46) :5965-5968