MISC

2014年2月

Metal Homoenolates

Comprehensive Organic Synthesis: Second Edition
  • M. Kimura

2
開始ページ
606
終了ページ
628
記述言語
英語
掲載種別
DOI
10.1016/B978-0-08-097742-3.00216-0
出版者・発行元
Elsevier Ltd.

Homoenolate represents a three-carbon synthon containing β-anionic carbon to provide a wide variety of alcohols by addition to carbonyl compounds. β-Zincio esters undergo a three-component coupling with carbon monoxide and allyl esters to furnish unsymmetrical ketones in the presence of Pd-catalyst. Enantiomerically enriched, 1-heteroatom-substituted allyl lithium species serve as homoenolate equivalents and are applicable to the synthesis of chiral γ-hydroxy ketones. The addition of N-heterocyclic carbene catalyst to α,β-unsaturated aldehydes can generate homoenolate equivalents to accomplish the enal-aldehyde annulation in order to give γ-butyrolactones. π-Allylpalladium treated with triethylborane, diethylzinc, and trialkylstannane achieves the nucleophilic allylation of carbonyl compounds to provide homoallyl alcohols and γ-butyrolactones. Ni-catalyzed homoallylation of carbonyls with conjugated dienes can formally play as homoaldol reaction to afford bis-homoallyl alcohols with excellent regio- and stereoselectivity. © 2014 Elsevier Ltd. All rights reserved.

リンク情報
DOI
https://doi.org/10.1016/B978-0-08-097742-3.00216-0
URL
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84903492792&origin=inward
ID情報
  • DOI : 10.1016/B978-0-08-097742-3.00216-0
  • SCOPUS ID : 84903492792

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