CONVENIENT FLUORIDE-MEDIATED REACTIONS OF LACTONES WITH SILYL KETENE ACETALS

被引：8

作者：

CSUK, R

SCHAADE, M

机构：

[1] Pharmazeutisch-Chemisches Institut, Universität Heidelberg, D-69120 Heidelberg

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 49期

关键词：

TASF; ALDOLISATION REACTIONS; SILYL KETENE ACETALS; LACTONES; CARBOHYDRATES;

D O I：

10.1016/S0040-4039(00)61507-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldolisation reactions of silyl ketene acetals with lactone carbonyls can be performed under very mild conditions in good yields in the presence of 5-10 mol-% of TASF.

引用

页码：7907 / 7910

页数：4

共 28 条

[1]

AINSWORTH C, 1971, J CHEM SOC CHEM COMM, P136

[2]

Cohen N., 1985, ORG SYNTH, V63, P127

[3] ACTIVATION OF SILICON HYDROGEN, SILICON OXYGEN, SILICON NITROGEN BONDS IN HETEROGENEOUS PHASE - SOME NEW METHODS IN ORGANIC-SYNTHESIS [J].

CORRIU, RJP ;

PERZ, R ;

REYE, C .

TETRAHEDRON, 1983, 39 (06) :999-1009

[4] CHAIN ELONGATION OF ALDONOLACTONES [J].

CSUK, R ;

GLANZER, BI .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (06) :809-822

[5] UNIQUE STEREOCONTROL IN LANTHANIDE(III)-CATALYZED ALDOL REACTIONS WITH THE KETENE SILYL ACETAL OF METHYL (R)-3-HYDROXYBUTANOATE [J].

GU, JH ;

TERADA, M ;

MIKAMI, K ;

NAKAI, T .

TETRAHEDRON LETTERS, 1992, 33 (11) :1465-1468

[6] GROUP TRANSFER POLYMERIZATION WITH POLY-UNSATURATED ESTERS AND SILYL POLYENOLATES [J].

HERTLER, WR ;

RAJANBABU, TV ;

OVENALL, DW ;

REDDY, GS ;

SOGAH, DY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5841-5853

[7] STEREOSELECTIVE SYNTHESES OF ALPHA-SUBSTITUTED CYCLIC ETHERS AND SYN-1,3-DIOLS [J].

HOMMA, K ;

TAKENOSHITA, H ;

MUKAIYAMA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (07) :1898-1915

[8] STEREOCHEMICAL CONTROL IN THE ESTER ENOLATE CLAISEN REARRANGEMENT .1. STEREOSELECTIVITY IN SILYL KETENE ACETAL FORMATION [J].

IRELAND, RE ;

WIPF, P ;

ARMSTRONG, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :650-657

[9] DIASTEREOSELECTIVITY IN THE DIRECTED ALDOL CONDENSATION OF 2-TRIMETHYLSILOXYFURAN WITH ALDEHYDES - A STEREODIVERGENT ROUTE TO THREO-DELTA-HYDROXY-GAMMA-LACTONES AND ERYTHRO-DELTA-HYDROXY-GAMMA-LACTONES [J].

JEFFORD, CW ;

JAGGI, D ;

BOUKOUVALAS, J .

TETRAHEDRON LETTERS, 1987, 28 (35) :4037-4040

[10] KETEN SILYL ACETAL CHEMISTRY .1. SIMPLE SYNTHESIS OF METHYL JASMONATE AND RELATED-COMPOUNDS BY UTILIZING KETEN METHYL DIMETHYL-T-BUTYLSILYL ACETAL [J].

KITA, Y ;

SEGAWA, J ;

HARUTA, JI ;

YASUDA, H ;

TAMURA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (04) :1099-1104

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