シライ　トモヒコ   Shirai Tomohiko   白井　智彦    所属   東邦大学  理学部 化学科    職種   講師
論文種別	原著
言語種別	英語
査読の有無	査読あり
表題	Rhodium-Catalyzed 1,4-Addition of Lithium 2-Furyltriolborates to Unsaturated Ketones and Esters for Enantioselective Synthesis of gamma-Oxo-Carboxylic Acids By Oxidation of the Furyl Ring with Ozone
掲載誌名	正式名：Chemistry - An Asian Journal ISSNコード：1861-4728
出版社	WILEY-V C H VERLAG GMBH
巻・号・頁	6(3),pp.932-937
著者・共著者	Xiao-Qiang Yu,Tomohiko Shirai,Yasunori Yamamoto,Norio Miyaura
担当区分	2nd著者
発行年月	2011/03
概要	Rhodium-catalyzed 1,4-addition of lithium 5-methyl-2-furyltriolborate ([ArBACHTUNGTRENUNG(OCH2)(3)CCH3] Li, Ar = 5-methyl-2-furyl) to unsaturated ketones to give beta-furyl ketones was followed by ozonolysis of the furyl ring for enantioselective synthesis of gamma-oxo-carboxylic acids. [RhACHTUNGTRENUNG(nbd)(2)]BF4 (nbd = 2,5-norbornadiene) chelated with 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (binap) or 2,3-bis(diphenylphosphino) butane (chiraphos) gave high yields and high selectivities in a range of 91-99% ee at 30 degrees C in a basic dioxane/water solution. The corresponding reaction of unsaturated esters, such as methyl crotonate, had strong resistance under analogous conditions, but the 1,4-adduct was obtained in 70% yield and with 94% ee when more electron-deficient phenyl crotonate was used as the substrate.
DOI	10.1002/asia.201000589