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Vol. 29 No. 12 (2017): Vol 29 Issue 12

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Synthesis of cis and trans 2,4,6-Tetrahydropyranols via Prins-Type Cyclization and Mitsunob Inversion

https://doi.org/10.14233/ajchem.2017.20882
N. Maruthi Raju
Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Limited, Bollaram Road, Miyapur, Hyderabad-500 049, India; Department of Organic Chemistry, Foods, Drugs and Water andhra University, Visakhapatnam-530 003, India
J. Moses Babu
Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Limited, Bollaram Road, Miyapur, Hyderabad-500 049, India
B. Venkateswara Rao
Department of Organic Chemistry, Foods, Drugs and Water andhra University, Visakhapatnam-530 003, India

Corresponding Author(s) : N. Maruthi Raju

raju1001@gmail.com

Asian Journal of Chemistry, Vol. 29 No. 12 (2017): Vol 29 Issue 12

Abstract

Prins cyclization of substituted homoallylic alcohol with aryl/aliphatic aldehyde in the presence of a boron trifluoride etherate and trifluoro acetic acid followed by hydrolysis of the resulting trifluoroacetate give substituted cis 2,4,6-tetrahydropyranol products 1-5(c), then Mitsunobu inversion subsequent methanolysis furnished trans 2,4,6-tetrahydropyranol products 1-5(d) stereoselectively in good yield. Our present work reports the synthesis and characterization of these 1-5(c,d) products.

Keywords

Prins cyclization Mitsunobu reaction Tetrahydropyranols Lewis acid Homoallylic alcohols
Raju, N. M., Babu, J. M., & Rao, B. V. (2017). Synthesis of cis and trans 2,4,6-Tetrahydropyranols via Prins-Type Cyclization and Mitsunob Inversion. Asian Journal of Chemistry, 29(12), 2771–2775. https://doi.org/10.14233/ajchem.2017.20882
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