Add time:08/09/2019         Source:sciencedirect.com

Chemoselective reduction of the carbonyl group in α-acyl-N-[Bis(methylthio)methylene]-alaninates 1a-c and phenylalaninates 1d,e allowed for the diastereoselective synthesis of both the syn and the anti isomers of the corresponding N-protected α,α-disubstituted β-hydroxy-α-amino esters 2. The stereochemistry of the process was tuned by switching between chelation-controlled and non-chelation-controlled conditions for the reduction. Compounds 2 can be transformed into the corresponding N-unprotected α-quaternized β-hydroxy-α-amino esters 4.

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