Journal of Organic Chemistry p. 993 - 994 (1993)
Update date:2022-07-29
Topics:
Xiang, Yi Bin
Snow, Ken
Belley, Michel
A method for preparation of enantiomerically pure α-hydroxy esters by stereoselective reduction of chiral α-keto esters under convenient conditions (LiAlH(OCEt3)3, THF, 0 deg C) has been developed.The compounds exo,exo-3-(arylsulfonamido)-2-borneol and exo,exo-2-(arylsulfonamido)-3-borneol have been used as novel auxiliaries to achieve highly diastereoselective reductions.The auxiliaries can be removed by mild saponification (LiOH, THF-H2O, rt) without racemization of the reduced products.
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