HIGH DIASTEREOFACIAL SELECTIVITY IN THE REACTION OF SILYL ENOL ETHERS WITH CHLOROSULFIDES

被引：8

作者：

IQBAL, J

SHUKLA, A

机构：

[1] Dept. of Chemistry, Indian Institute of Technology, Kanpur

来源：

TETRAHEDRON | 1991年 / 47卷 / 41期

关键词：

D O I：

10.1016/S0040-4020(01)96197-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chlorosulfides 1 or 2 react with silyl enol ethers in presence of anhydrous zinc bromide to give mainly the corresponding syn products 4 or 6 respectively. The high syn selectivity of these reaction is explained by nucleophilic addition to a Chelated Chiral thionium ion.

引用

页码：8753 / 8766

页数：14

共 39 条

[1] A NEW ACYLATION CATALYST
AHMAD, S
IQBAL, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (02) : 114 - 115
[2] AHMAD S, 1988, SYNTHETIC COMMUN, V14, P1679
[3] ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .3. ON THE STEREOCHEMISTRY OBSERVED IN THE CYCLIZATION OF CHIRAL ACETALS OF POLYOLEFINIC ALDEHYDES - FORMATION OF OPTICALLY-ACTIVE HOMOALLYLIC ALCOHOLS
BARTLETT, PA
JOHNSON, WS
ELLIOTT, JD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) : 2088 - 2089
[4] GENERATION OF CARBON-CARBON DOUBLE-BONDS FROM BETA-OXYGENATED PHENYLSELENO, PHENYLTHIO, AND IODO SPECIES - A NEW USE FOR THE CHLOROTRIMETHYLSILANE-SODIUM IODIDE REAGENT
CLIVE, DLJ
KALE, VN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) : 231 - 234
[5] A CONCISE AND STEREOSELECTIVE ROUTE TO THE PREDOMINANT STEREOCHEMICAL PATTERN OF THE TETRAHYDROPYRANOID ANTIBIOTICS - AN APPLICATION TO INDANOMYCIN
DANISHEFSKY, SJ
DENINNO, S
LARTEY, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) : 2082 - 2089
[6] THE TOTAL SYNTHESIS OF THE AGLYCON OF AVERMECTIN-A1A
DANISHEFSKY, SJ
ARMISTEAD, DM
WINCOTT, FE
SELNICK, HG
HUNGATE, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) : 8117 - 8119
[7] DANISHEFSKY SJ, 1982, J ORG CHEM, V37, P3803
[8] THE METHOXYCARBONYLALKYLATION AND METHOXYCARBONYLALKYLIDENATION OF SILYL ENOL ETHERS
FLEMING, I
IQBAL, J
[J]. TETRAHEDRON LETTERS, 1983, 24 (03) : 327 - 328
[9] ALPHA-GAMMA-RATIOS IN PHENYLTHIOMETHYLATION OF SILYL DIENOL ETHERS
FLEMING, I
IQBAL, J
[J]. TETRAHEDRON LETTERS, 1983, 24 (28) : 2913 - 2916
[10] THE GAMMA-ALKYLATION OF ENONES USING SILYL DIENOL ETHERS - THE EFFECT OF CHANGING THE ELECTROPHILE AND OF CHANGING THE SILYL GROUP
FLEMING, I
LEE, TV
[J]. TETRAHEDRON LETTERS, 1981, 22 (07) : 705 - 708

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