SYNTHESES VIA VINYL SULFONES .44. BIS-ALKYLATION OF DIMETALLATED PHENYLSULFONYLMETHYL TRIFLONE - A N+1 ANNULATION STRATEGY FOR SYNTHESIS OF CYCLIC VINYL SULFONES

被引：18

作者：

MAGAR, SS ^{[1
]}

FUCHS, PL ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 06期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)77705-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bis-metallation of phenylsulfonylmethyl triflone 4b produces a geminal dianion which can be dialkylated to afford alpha-phenylsulfonyl triflones. Treatment of these compounds with DBU affords vinyl sulfones which can be isomerized to allyl sulfones.

引用

页码：745 / 748

页数：4

共 30 条

[1]

BRAISH TF, 1986, CHEM REV, V86, P903

[2] A NEW SYNTHETIC METHOD FOR THE PREPARATION OF 2,8-DISUBSTITUTED OXOCANE DERIVATIVES - SYNTHESIS OF LAUTHISAN AND LAURENAN [J].

CARLING, RW ;

HOLMES, AB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (07) :565-567

[3]

CASTRO A, 1990, 199TH ACS NAT M BOST

[4] NEW APPLICATIONS OF 2,3-BIS (BROMOMETHYL)-1,3-BUTADIENE - ACCESS TO 1,2-BIS(METHYLENE)CYCLOPENTANES, TO 2H-ISOINDOLES AND TO 2,3-DITHIANAPHTHALENES [J].

COMMERCON, A ;

PONSINET, G .

TETRAHEDRON LETTERS, 1985, 26 (34) :4093-4096

[5] AN EFFICIENT SYNTHESIS OF BOTH ENANTIOMERS OF TRANS-1,2-CYCLOPENTANEDIOL AND THEIR CONVERSION TO 2 NOVEL BIDENTATE PHOSPHITE AND FLUOROPHOSPHINITE LIGANDS [J].

CUNNINGHAM, AF ;

KUNDIG, EP .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1823-1825

[6] IMPROVED SELECTIVITY IN THE PREPARATION OF SOME 1,1-DIFUNCTIONALIZED 3-CYCLOPENTENES - HIGH-YIELD SYNTHESIS OF 3-CYCLOPENTENECARBOXYLIC ACID [J].

DEPRES, JP ;

GREENE, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) :928-931

[7]

HENDRICKSON JB, 1984, SYNTHESIS-STUTTGART, P320

[8] TRIFLONES (CF3SO2C) - SURVEY OF REACTIVITY AND SYNTHETIC UTILITY [J].

HENDRICKSON, JB ;

GIGA, A ;

WAREING, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (07) :2275-2276

[9] MILD CONVENIENT SYNTHESIS OF ALPHA-METHYLENE SULFONES [J].

HENDRICKSON, JB ;

PALUMBO, PS .

TETRAHEDRON LETTERS, 1985, 26 (24) :2849-2852

[10] A NEW SYNTHESIS OF CYCLOPENTENONES - DIHYDROJASMONE [J].

HENDRICKSON, JB ;

PALUMBO, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) :2110-2112

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