Sahu Samrat, Karan Ganesh, Roy Lisa, Maji Modhu Sudan
Department of Chemistry, Indian Institute of Technology Kharagpur Kharagpur 721302 India
Institute of Chemical Technology Mumbai, IOC Odisha Campus Bhubaneswar Bhubaneswar 751013 India.
Chem Sci. 2022 Jan 28;13(8):2355-2362. doi: 10.1039/d1sc06259j. eCollection 2022 Feb 23.
A diastereoselective allylation of -butane sulfinyl α-iminoesters using allylboronic acids is developed to obtain optically active non-proteinogenic α-amino acid precursors in good yields and diastereoselectivities. Gram-scale synthesis, broad tolerance of functional groups, excellent stereodivergence, post-synthetic modifications, and easy removal of the chiral auxiliary are some of the key highlights. The protocol is applicable to various amino acids and short peptides, resulting in the incorporation of these precursors at the N-terminal position.
利用烯丙基硼酸对丁烷亚磺酰基α-亚氨基酯进行非对映选择性烯丙基化反应，以良好的产率和非对映选择性获得光学活性的非蛋白质ogenicα-氨基酸前体。克级规模的合成、对官能团的广泛耐受性、出色的立体发散性、合成后修饰以及手性助剂的易于去除是一些关键亮点。该方案适用于各种氨基酸和短肽，可将这些前体引入N端位置。
