Regio- and Stereocontrolled Synthesis of Allenic and Acetylenic Derivatives. Organotitanium and Boron Reagents

Regio- and Stereocontrolled Synthesis of Allenic and Acetylenic Derivatives. Organotitanium and Boron Reagents
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六烯和乙炔衍生物的区域和立体控制合成。

DOI:
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发表时间:
1984
期刊:
影响因子:
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通讯作者:
Hisashi Yamamoto
Hisashi Yamamoto
中科院分区:
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文献类型:
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作者:
K. Furuta*;M. Ishiguro;Ryuichi Haruta;N. Ikeda;Hisashi Yamamoto

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由1-烷基丙炔衍生的炔丙基钛试剂与醛缩合,区域选择性地生成α-联烯醇,而由1-烷基-1-丁炔衍生物生成的联烯基钛试剂则具有较高的区域和立体选择性生成苏式-β-炔醇。反应过程由起始炔的取代模式决定。研究了1,3-双(三烷基硅基)丙炔或(三烷基硅基)乙腈与醛的类似反应。
The propargyltitanium reagents derived from 1-alkylpropyne condensed with aldehydes to give α-allenyl alcohol regioselectively, while the allenyltitanium reagents generated from 1-alky1-1-butyne derivatives gave threo-β-acetylenic alcohols with high regio- and stereoselectivities. The course of the reaction was determined by the substitution pattern of starting alkynes. The similar reactions of metallated 1,3-bis(trialkylsilyl)propyne or (trialkylsilyl)acetonitrile with aldehydes were also investigated.