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  • Asymmetric synthesis of cyclopropylamines starting from N-sulfinyl alpha-chloro ketimines.

Asymmetric synthesis of cyclopropylamines starting from N-sulfinyl alpha-chloro ketimines.

Organic letters (2007-01-16)
Bram Denolf, Sven Mangelinckx, Karl W Törnroos, Norbert De Kimpe
要旨

Treatment of novel chiral N-sulfinyl alpha-chloro ketimines with Grignard reagents resulted in the synthesis of chiral N-(1-substituted cyclopropyl)-tert-butanesulfinamides in acceptable to good yields and diastereoselectivity via 1,3-dehydrohalogenation and subsequent addition of the Grignard reagent to the intermediate cyclopropylideneamine. Only in the case of allylmagnesium chloride did the reaction lead to aziridines in high yield. Further deprotection toward N-unprotected 1-substituted cyclopropylamines was established, and the absolute configuration was determined. [reaction: see text].

材料
製品番号
ブランド
製品内容

Sigma-Aldrich
シクロプロピルアミン, 98%
カタログ番号
容量
在庫状況
単価
数量