SYNTHESIS OF A NOVEL 4-CARBON CHIRON - (R)-1-TERT-BUTYLDIMETHYLSILYL-3,4-EPOXY-BUT-1-YNE

被引：11

作者：

LOPP, M ^{[1
]}

KANGER, T ^{[1
]}

MURAUS, A ^{[1
]}

PEKH, T ^{[1
]}

LILLE, U ^{[1
]}

机构：

[1] ACAD SCI ESSSR, INST CHEM & BIOL PHYS, TALLINN 200001, ESTONIA, USSR

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(00)86131-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple and efficient synthesis of the novel chiron-(R)-1-TBDMS-3,4-epoxy-but-1-yne has been developed starting from a derivative of (R,R)-(+)-tartaric acid. A new stereoselective bromination reaction of an O-silyl ether with BBr3 is also described.

引用

页码：943 / 944

页数：2

共 16 条

[1]

ADAM G, 1988, SYNTHESIS-STUTTGART, P373

[2] A 2-STEP SYNTHESIS OF (R)-BENZYLGLYCIDYL AND (S)-BENZYLGLYCIDYL ETHER [J].

BYUN, HS ;

BITTMAN, R .

TETRAHEDRON LETTERS, 1989, 30 (21) :2751-2754

[3] ENZYMATIC ROUTES TO ENANTIOMERICALLY ENRICHED 1-BUTENE OXIDE [J].

CHENAULT, HK ;

KIM, MJ ;

AKIYAMA, A ;

MIYAZAWA, T ;

SIMON, ES ;

WHITESIDES, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2608-2611

[4] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[5] 1,4-BISMETHANESULFONATES OF STEREOISOMERIC BUTANETETRAOLS + RELATED COMPOUNDS [J].

FEIT, PW .

JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (01) :14-+

[6]

GRUBER L, 1975, SYNTHESIS-STUTTGART, P708

[7]

KANG SK, 1990, SYNLETT, P591

[8]

KANGER TP, 1990, ZH ORG KHIM+, V26, P1711

[9] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[10]

LOPP M, 1990, 8TH INT C ORG SYNTH, P235

← 1 2 →