Chemo- and Diasteroselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-alpha-amino Aldehydes

摘要

N-Boc-alpha-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.