書誌事項
- タイトル別名
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- Highly Selective Organic Synthesis via Organic “Ate” Complexes
- アート サクタイ ate complex オ モチイル コウ センタクテキ ユ
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The development of several new procedures for highly selective organic synthesis via organic “ate” complexes including lithium, copper, boron, aluminum, and palladium is described. Dialkenylchloroboranes (1) react with 3 molar equivalents of methylcopper to produce symmetrical (E, E) -1, 3-dienes in high yields. It is revealed that the reaction involves the alkenylcopper-boron complex (loose “ate” complex), free alkenylcopper, and/or copper alkenylborate (tight “ate” complex) as the intermediates. These intermediates further react with allylic halides or alkyl halides to produce stereoselectively E-1, 4-dienes or olefins, respectively. New organocopper reagents, such as RCu·BF3 and RCu·BR3, are developed. Complete γ-attack toward allylic halides, direct alkylation of alcohols, and 1, 4-addition to previously unreactive substituted enoate esters and enoic acids are realized by using the former reagent. Stereocontrolled cis-addition to α, β-acetylenic carbonyl derivatives is achieved by using the latter reagent. Regiocontrolled head-to-tail coupling of allylic boron “ate” complexes with allylic halides is accomplished. Complete control to the regiochemistry in the reaction of heteroatom substituted allylic carbanions is realized with the allylic aluminum “ate” complexes which are formed by the addition of triethylaluminum to the carbanions. The stereoselective olefin synthesisvia the reaction of alkenylboranes with palladium acetate is developed.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 37 (8), 641-654, 1979
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205313165568
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- NII論文ID
- 130000924006
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 2061793
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
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- 抄録ライセンスフラグ
- 使用不可