DIASTEREOSELECTIVE ADDITION OF VINYL ORGANOMETALLIC REAGENTS TO L-SERINAL

被引：89

作者：

COLEMAN, RS

CARPENTER, AJ

机构：

[1] Department of Chemistry, Biochemistry University of South Carolina, Columbia

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 13期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)91709-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An examination of the diastereoselective addition of vinyl organometallic reagents to N-BOC L-serinal acetonide (1) to afford mixtures of syn-2 and anti-2 is presented. Vinylzinc chloride in nonpolar solvents was found to add to the aldehyde carbonyl of 1 with 6:1 syn/anti stereoselectivity in excellent yields.

引用

页码：1697 / 1700

页数：4

共 27 条

[1] AHN NT, 1980, TOP CURR CHEM, V88, P145
[2] SYNTHESIS OF ENANTIOMERICALLY PURE 2,3-DIDEOXY-HEPT-2-ENONO-1,4-LACTONE DERIVATIVES VIA DIASTEREOSELECTIVE ADDITION OF 2-(TRIMETHYLSILOXY)FURAN TO D-GLYCERALDEHYDE AND D-SERINAL-BASED 3-CARBON SYNTHONS
CASIRAGHI, G
COLOMBO, L
RASSU, G
SPANU, P
[J]. TETRAHEDRON LETTERS, 1989, 30 (39) : 5325 - 5328
[3] SYNTHESIS OF 1-(2-HYDROXYARYL)-1,2,3-PROPANETRIOL AND 1-(2-HYDROXYARYL)-2-AMINO-1,3-PROPANEDIOL DERIVATIVES OF EITHER THREO OR ERYTHRO CONFIGURATION
CASIRAGHI, G
CORNIA, M
RASSU, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) : 4919 - 4922
[4] HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF 6-DEOXY-6-AMINOHEPTOPYRANURONIC ACID-DERIVATIVES
CASIRAGHI, G
COLOMBO, L
RASSU, G
SPANU, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (08) : 603 - 604
[5] CASIRAGHI G, 1990, TETRAHEDRON, V55, P3772
[6] CHEREST M, 1968, TETRAHEDRON LETT, P2199
[7] COLEMAN RS, UNPUB
[8] A DIVERGENT ROUTE TO NOJIRIMYCIN ANALOGS FROM L-SERINAL AND 2-ACETYLTHIAZOLE
DONDONI, A
FANTIN, G
FOGAGNOLO, M
MERINO, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (12) : 854 - 856
[9] STEREOSELECTIVE MONO-HOMOLOGATION AND BIS-HOMOLOGATION OF L-SERINAL VIA 2-TRIMETHYLSILYLTHIAZOLE ADDITION - THE THIAZOLE ROUTE TO AMINO L-SUGARS AND D-ERYTHRO-SPHINGOSINES
DONDONI, A
FANTIN, G
FOGAGNOLO, M
MEDICI, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (01) : 10 - 12
[10] STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES
DONDONI, A
FANTIN, G
FOGAGNOLO, M
PEDRINI, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) : 1439 - 1446

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