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Diastereoselective reduction of α-acyl-N-[Bis(methylthio)methylene]alaninates and phenylalaninates: Synthesis of α,α-disubstituted β-hydroxy α-amino esters

✍ Scribed by Carlos Alvarez-Ibarra; Aurelio G Csákÿ; M Luz Quiroga; Dolores Ramírez

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
475 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Chemoselective reduction of the carbonyl group in ~-acyl-N-[Bis(methylthio)methylene]alaninates la--¢ and phenylalaninates I d,e allowed for the diastereoselective synthesis of both the syn and the anti isomers of the corresponding N-protected ot,a-disubstituted [3-hydroxy-ot-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 o~-quaternized I~-hydroxy-c~-amino esters 4.

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