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Synlett 2001; 2001(9): 1431-1433
DOI: 10.1055/s-2001-16774
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Diastereoselective Synthesis of 1-Allyl and 1,2-bis(Allyl)-1,2-diols: Versatile Synthons For Substituted Tetrahydrofuran Derivatives

Subodh Kumar* , Pervinder Kaur, Swapandeep Singh Chimni, Palwinder Singh
  • *Department of Chemistry, Guru Nanak Dev University, Amritsar - 143 005, India; E-mail: subodh.kumar@angelfire.com
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Publication History

Publication Date:
28 August 2001 (online)

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2-Hydroxyketones and 2-ketoaldehydes undergo indium mediated highly diastereoselective mono and bis- allylation reactions to give respective 1-allyl 2a-c and 1,2-bis (allyl)-7a-c 1,2-diols. 2a undergoes I2/NaHCO3 and m-CPBA mediated diastereoselective intramolecular cyclizations to provide respective (2S*,3R*,5S*)-2,3-diphenyl-4-hydroxy-5-iodo methyltetrahydrofuran 4a and (2S*,3R*,5R*)-2,3-diphenyl-4-hydroxy-5-hydroxymethyl tetrahydrofuran 5b as major product.

diastereoselective - allylation - cyclisation - hydroxyketones - ketoaldehydes

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