Chemo- and Diastereoselective N -Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N -Boc-α-amino Aldehydes

作者：Pouyan Haghshenas, Michel Gravel · 发表于：Organic Letters · 年份：2016 · DOI：10.1021/acs.orglett.6b02123 · 被引用次数：45 · 研究领域：N-Heterocyclic Carbenes in Organic and Inorganic Chemistry、Synthesis of heterocyclic compounds、Synthetic Organic Chemistry Methods

N-Boc-α-amino aldehydes are shown to be excellent partners in cross-benzoin reactions with aliphatic or heteroaromatic aldehydes. The chemoselectivity of the reaction and the facial selectivity on the amino aldehyde allow cross-benzoin products to be obtained in good yields and good diastereomeric ratios. The developed method is utilized as the key step in a concise total synthesis of d-arabino-phytosphingosine.