Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines

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• 作者：Lukas Werner ; Jason Reed Hudlicky ; Martina Wernerova ; Tomas Hudlicky
• 关键词：Oxazines ; 1 ; 2-Amino alcohols ; 1 ; 4-Amino alcohols ; Hetero Diels– ; Alder reaction ; Oxazolines
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：22 May 2010
• 年：2010
• 卷：66
• 期：21
• 页码：3761-3769
• 全文大小：961 K

文摘

Conjugated dienes were converted to 1,2-oxazines by reaction with an acyl nitroso dienophile. The oxazines were reduced to 1,4-N-acetylamino alcohols, which were rearranged to the corresponding oxazolines upon treatment with methanesulfonyl chloride or anhydride. The oxazolines yielded 1,2-N-acetylamino alcohols upon hydrolysis. Thus either 1,4- or 1,2-N-acetylamino alcohols are available from 1,3-dienes via this methodology. Experimental and spectral data are provided for all new compounds.