顺式和反式1,2-氨基醇的高度立体选择性合成。
Highly stereoselective syntheses of syn- and anti-1,2-amino alcohols.
作者信息
Hoffman Robert V, Maslouh Najib, Cervantes-Lee Francisco
机构信息
Department of Chemistry and Biochemistry, North Horseshoe Drive, New Mexico State University, Las Cruces, New Mexico 88003-8001, USA.
出版信息
J Org Chem. 2002 Feb 22;67(4):1045-56. doi: 10.1021/jo010270f.
The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-Bu)3 in ethanol at -78 degrees C. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)3 in THF at -5 degrees C.
N-保护的氨基酮的还原反应可以立体选择性地进行，以生成顺式或反式氨基醇非对映异构体。氨基甲酸酯保护的氨基酮在-78℃的乙醇中用LiAlH(O-t-Bu)3可以可预测地、选择性地还原为反式氨基醇。N-三苯甲基保护的氨基酮在-5℃的四氢呋喃中用LiAlH(O-t-Bu)3可以选择性地还原为顺式氨基醇。
Zotero 插件