Stereoselective synthesis of syn,syn- and syn,anti-1,3,5-triols via intramolecular hydrosilylation of substituted pent-3-en-1,5-diols.
A stereoselective method for synthesis of syn,syn- and syn,anti-1,3,5-triols based on a double allylboration-intramolecular hydrosilylation sequence has been developed. The 1,3-syn stereocontrol is achieved in the intramolecular hydrosilylation of monoprotected (Z)-1,5-syn-diols and (E)-1,5-anti-diols with 87:13 to 95:5 and 86:14 to 88:12 diastereomeric ratios, respectively, by using 0.5 mol % of Karstedt's catalyst in toluene.
Li
Fangzheng
F
Department of Chemistry, Scripps-Florida, Jupiter, Florida 33458, USA.
Roush
William R
WR
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D012821:Silanes