Stereoselective Synthesis of anti-N-Protected 3-Amino-1,2-epoxides by Nucleophilic Addition to N-tert-Butanesulfinyl Imine of a Glyceraldehyde Synthon

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• 作者：Scott S. Harried ; Michael D. Croghan ; Matthew R. Kaller ; Patricia Lopez ; Wenge Zhong ; Randall Hungate ; Paul J. Reider
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：August 21, 2009
• 年：2009
• 卷：74
• 期：16
• 页码：5975-5982
• 全文大小：907K
• 年卷期：v.74,no.16(August 21, 2009)
• ISSN：1520-6904

文摘

A di-O-TBS protected glyceraldehyde synthon was condensed with Ellman’s reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction of various R groups. The Ellman adducts were converted to useful multifunctional intermediates 18a−i in one pot. The alcohols 18a−i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2-epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.