Unexpected reversal of stereochemistry observed in the addition of methallyltrimethylsilane to a chiral α-keto imide.

A Lewis acid-promoted nucleophilic addition of methallyltrimethylsilane to a chiral α-keto imide proceeded with stereoselectivity opposite to that predicted from Soai's report. The difference in the structure of α-keto imides between Soai's and our cases might have affected the diastereofacial selectivity. © The Author(s) 2021. Published by Oxford University Press on behalf of Japan Society for Bioscience, Biotechnology, and Agrochemistry.

Citation

Sayaka Ishii, Katsuya Saito, Shigefumi Kuwahara, Masaru Enomoto. Unexpected reversal of stereochemistry observed in the addition of methallyltrimethylsilane to a chiral α-keto imide. Bioscience, biotechnology, and biochemistry. 2021 Feb 24;85(3):488-492

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PMID: 33624787

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