2014年2月
Metal Homoenolates
Comprehensive Organic Synthesis: Second Edition
- 巻
- 2
- 号
- 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
- ID情報
-
- DOI : 10.1016/B978-0-08-097742-3.00216-0
- SCOPUS ID : 84903492792