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

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

Chemical communications (Cambridge, England) (2002-07-19)
Kwan Soo Kim, Yong Joo Lee, Jin Hwan Kim, Da Kyung Sung
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Bromo-2-pentene, predominantly trans, 95%