A Useful Allene for the Stereoselective Synthesis of Protected Quaternary 2-Amino-2-vinyl-1,3-diols
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- 作者：Aleix Rodríguez ; Xavier ArizaMiguel A. Contreras ; Jordi Garcia ; Paul Lloyd-WilliamsNerea Mercadal ; Carolina Sánchez
- 刊名：Journal of Organic Chemistry
- 出版年：2017
- 出版时间：February 3, 2017
- 年：2017
- 卷：82
- 期：3
- 页码：1851-1855
- 全文大小：321K
- ISSN：1520-6904
文摘
Treatment of readily available allene 1 with Cy2BH followed by addition of an aldehyde led to quaternary protected 2-amino-2-vinyl-1,3-diols in high yield and excellent stereochemical purity. The choice of benzoyl as N-protecting group is critical since the observed N- to O-Bz transfer during the process prevents later undesired isomerizations in the adducts and keeps all heteroatoms protected.