HIGHLY ENANTIOSELECTIVE SYNTHESIS OF PROPARGYL ALCOHOLS

被引：21

作者：

HARTLEY, RC ^{[1
]}

LAMOTHE, S ^{[1
]}

CHAN, TH ^{[1
]}

机构：

[1] MCGILL UNIV,DEPT CHEM,MONTREAL H3A 2K6,QUEBEC,CANADA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)60315-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silylpropargyl carbanions bearing a chiral auxiliary on silicon have been alkylated with excellent regio and diastereoselectivity. The effect of the solvent has been investigated and propargyl alcohols have been synthesised in high enantiomeric excess.

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页码：1449 / 1452

页数：4

相关论文

共 13 条

[1] ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP [J].

BURGESS, K ;

JENNINGS, LD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6129-6139

[2] CHIRAL ORGANO-SILICON COMPOUNDS IN SYNTHESIS - HIGHLY ENANTIOSELECTIVE SYNTHESIS OF ARYLCARBINOLS [J].

CHAN, TH ;

PELLON, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8737-8738

[3] CHIRAL ORGANOSILICON COMPOUNDS IN ASYMMETRIC-SYNTHESIS [J].

CHAN, TH ;

WANG, D .

CHEMICAL REVIEWS, 1992, 92 (05) :995-1006

[4] ALKYLMETAL ASYMMETRIC REDUCTION .17. STEREOCHEMICAL COURSE OF KETONE REDUCTION BY BETA-BRANCHED ALKYL DERIVATIVES OF BERYLLIUM AND ALUMINUM [J].

FALORNI, M ;

LARDICCI, L ;

ROSINI, C ;

GIACOMELLI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (11) :2030-2033

[5] EFFECT OF SUBSTITUENT ON REACTIONS REMOTE FROM SILICON - REGIOSELECTIVE ALPHA-ALKYLATION OF ALPHA-SILYLALLYL CARBANIONS [J].

HORVATH, RF ;

CHAN, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) :317-327

[6] CHIRAL ORGANOSILICON COMPOUNDS IN SYNTHESIS - REGIOSELECTIVE AND STEREOSELECTIVE ALKYLATION OF A CHIRAL ALPHA-SILYLCINNAMYL CARBANION [J].

LAMOTHE, S ;

CHAN, TH .

TETRAHEDRON LETTERS, 1991, 32 (16) :1847-1850

[7]

LAMOTHE S, 1992, IN PRESS CAN J CHEM

[8] 2,6-DI-O-PENTYL-3-O-TRIFLUOROACETYL CYCLODEXTRIN LIQUID STATIONARY PHASES FOR CAPILLARY GAS-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS [J].

LI, WY ;

JIN, HL ;

ARMSTRONG, DW .

JOURNAL OF CHROMATOGRAPHY, 1990, 509 (02) :303-324

[9]

MARX KH, 1984, LIEBIGS ANN CHEM, P474

[10] REDUCTION OF ALPHA,BETA-ACETYLENIC KETONES WITH B-3-PINANYL-9-BORABICYCLO[3.3.1]NONANE - HIGH ASYMMETRIC INDUCTION IN ALIPHATIC SYSTEMS [J].

MIDLAND, MM ;

MCDOWELL, DC ;

HATCH, RL ;

TRAMONTANO, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :867-869