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Stereoselective Syntheses of Alcohols, XXIV. Synthesis of 2,6-Dideoxy-L-hexoses

✍ Scribed by Hoffmann, Reinhard W. ;Metternich, Rainer ;Lanz, Joachim W.

Publisher
John Wiley and Sons
Year
1987
Tongue
English
Weight
756 KB
Volume
1987
Category
Article
ISSN
0947-3440

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✦ Synopsis

bcnzyllactaldzhydc Icd 10 various 3,4,5-trioxygenatcd 1-hcxenes or w c i h i m . xylo. riho. and Iyxo configuration. The cxtcnt of asymrnctric induction wnnunted to 82: 18 (urahinoJxylo) in the addition ciC 3 and tn 4O:M) ( r i / w / / y . w ) on addition of 6. The factors which tlc!crininc thc dircction and cxtcnl of asymmetric induction are discussed, pointing to Cornforth-type conformations in thc transition S W I ~. Individual members of the 3.4,s-trioxygcnated hexcnts ~r r t converted into 2.6dideoxy-~-hexoses of aruhino. riho, 1

We obtained 97% of a 65: 35 mixture7319) of the knownz1) homoallyl alcohols 10 and 11. This time, the expected17) diastereomer was formed in preference.

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