A synthesis of statine utilizing an oxidative route to chiral. alpha.-amino aldehydes

…, CF Homnick, GS Ponticello, BE Evans

Index: Rittle, Kenneth E.; Homnick, Carl F.; Ponticello, Gerald S.; Evans, Ben E. Journal of Organic Chemistry, 1982 , vol. 47, # 15 p. 3016 - 3018

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Citation Number: 116

Abstract

3 (R'= Boc) 30 min gave aldehyde 3,(R'= Boc), again in good yield. Little information is available regarding the chiral stability of such a-amino aldehyde derivatives. l'Therefore, we have analyzed the optical purity and stability of samples of the aldehyde 3 (R'= Boc) taken immediately from the oxidation and samples stored at 0" C and at ambient temperature. The aldehyde samples were reduced with sodium borohydride to carbinol 4 and then oxidized ...