著者

吉良 満夫 海野 雅史 当麻 博文 百足 勉 河内 卓彌

出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.62, no.2, pp.162, 2004-02-01 (Released:2009-11-13)

著者

河内 卓彌 百足 勉 Jonathan A. Ellman

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.62, no.2, pp.128-139, 2004-02-01 (Released:2009-11-13)

参考文献数

43

被引用文献数

7 10

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tert-Butanesulfinyl imines are exceedingly versatile intermediates for the asymmetric synthesis of amines. Aldimines 15 and ketimines 16 are prepared in high yields under mild conditions by condensing enantiomerically pure tert-butanesulfinamide 10, either enantiomer of which is readily synthesized in large scale from inexpensive reagents, with a wide range of aldehydes and ketones. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition function as a versatile protecting group of the amines, which is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched amines, α, α-dibranched amines, α- and β-amino acids, 1, 2- and 1, 3-amino alcohols, and α-trifluoromethylamines are efficiently synthesized using this methodology.