Chemical Communications 2002-05-21

Synthesis of (+)-polyoxamic acid and D-sorbitol from simple achiral allylic halides employing (S,S)-hydrobenzoin as a chiral source.

Kwan Soo Kim, Yong Joo Lee, Jin Hwan Kim, Da Kyung Sung

Index: Chem. Commun. (Camb.) (10) , 1116-7, (2002)

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Abstract

Coupling of cis-1-bromo-2-pentene and (S,S)-hydrobenzoin stannylene acetal followed by regio- and stereoselective transformations of the resulting allylic ether gave (+)-polyoxamic acid and a similar procedure was applied to the synthesis of D-sorbitol from trans-1-iodo-2-hexene.