A novel route to fully substituted cyanoallenes from three components, ketones, chloromethyl p-tolyl sulfoxide, and nitriles, via α-bromocyclopropyl p-tolyl sulfoxides

被引：12

作者：

Satoh, T ^{[1
]}

Gouda, Y ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 16期

关键词：

allene; cyanoallene; sulfoxide; sulfoxide-lithium exchanged; lithium cyclopropylidene;

D O I：

10.1016/j.tetlet.2006.01.161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 1-chlorovinyl p-tolyl sulfoxides. which were derived front ketones and chloromethyl p-tolyl sulfoxide in high yields, with lithium alpha-carbanion of nitriles gave the adducts in quantitative yields. The adducts were converted to alpha-bromocyclopropyl p-tolyl sulfoxides in two steps in good yields. Finally, the sulfoxides were treated with excess lithium carbanion of isobutyronitrile to afford fully Substituted cyanoallenes in high to quantitative yields via sulfoxide-lithium exchange reaction. This procedure offers a novel synthetic method for fully substituted cyanoallenes with coupling of three components (ketones, chloromethyl p-tolyl sulfoxide, and nitriles) in good overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2835 / 2838

页数：4

共 45 条

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[23] The first synthesis of enantiomerically pure cyclopropylphosphonate analogues of nucleotides via asymmetric cyclopropanation of chiral (1-diethoxyphosphoryl)vinyl p-tolyl sulfoxide
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[25] ASYMMETRIC-SYNTHESIS OF PROTECTED ALPHA-HYDROXYALDEHYDES FROM ACYL CHLORIDES USING P-TOLYL P-TOLYLTHIOMETHYL SULFOXIDE AS CHIRAL CARBONYL SYNTHON
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[29] A novel synthesis of 2,4,4-trisubstituted 2-cyclopentenones by consecutive reaction of 1-chlorovinyl p-tolyl sulfoxides with acetonitrile and its homologues
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